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Activation of Otherwise Unreactive C-Cl Bonds

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Activation of Unreactive Bonds and Organic Synthesis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 3))

Abstract

During the past decade, considerable progress has been made in the area of transition metal-catalyzed cleavage and functionalization of the inert C-Cl bond in nonactivated chloroaromatic compounds. This new and important field of chemistry is reviewed in the present chapter, which describes both mechanistic and synthetic aspects of C-Cl activation. Oxidative addition reactions of chloroarenes to complexes of catalytic metals are discussed, along with their applications in a wide variety of reductive dechlorination, nucleophilic displacement, olefin arylation, coupling, and carbonylation reactions.

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References

  1. Grushin VV, Alper H (1994) Chem Rev 94:1047

    Article  CAS  Google Scholar 

  2. Rossi RA, de Rossi RH (1983) Aromatic substitution by the SRN1 mechanism. ACS, Washington DC

    Google Scholar 

  3. Lindley J (1984) Tetrahedron 40:1433.

    Article  CAS  Google Scholar 

  4. Sainsbury M (1980) Tetrahedron 36:3327.

    Article  CAS  Google Scholar 

  5. Fanta PE (1974) Synthesis 9.

    Google Scholar 

  6. Couture C, Paine AJ (1985) Can J Chem 63:111

    Article  CAS  Google Scholar 

  7. Miller J (1968) Aromatic nucleophilic substitution. Elsevier, New York

    Google Scholar 

  8. March J (1985) Advanced organic chemistry, 3rd edn. John Wiley and Sons, New York

    Google Scholar 

  9. Grushin VV (1992) Acc Chem Res 25:529.

    Article  CAS  Google Scholar 

  10. Grushin VV, Demkina II, Tolstaya TP (1991) Inorg Chem 30:1760.

    Article  CAS  Google Scholar 

  11. Tolstaya TP, Demkina II, Grushin VV, Vanchikov AN (1989) J Org Chem USSR 25:2305.

    Google Scholar 

  12. Grushin VV, Kantor MM, Tolstaya TP, Shcherbina TM (1984) Bull Acad Sci USSR Div Chem Sci 33:2130

    Article  Google Scholar 

  13. Kalinin VN (1987) Russ Chem Rev 56:682.

    Article  Google Scholar 

  14. Balas L, Jhurry D, Latxague L, Grelier S, Morel Y, Hamdani M, Ardoin N, Astruc D (1990) Bull Soc Chim Fr 401

    Google Scholar 

  15. Mutin R, Lucas C, Thivolle-Cazat J, Dufaud V, Dany F, Basset J-M (1988) J Chem Soc Chem Commun 896.

    Google Scholar 

  16. Dany F, Mutin R, Lucas C, Dufaud V, Thivolle-Cazat J, Basset J-M (1989) J Mol Catal 51:L15.

    Article  CAS  Google Scholar 

  17. Dufaud V, Thivolle-Cazat J, Basset J-M, Mathiew R, Jaud Z, Waissermann J (1991) Organometallics 10:4005.

    Article  CAS  Google Scholar 

  18. Carpentier JF, Petit F, Mor-treux A, Dufaud V, Basset J-M, Thivolle-Cazat J (1993) J Mol Catal 81:1.

    Article  CAS  Google Scholar 

  19. Carpentier J-F, Finet E, Castanet Y, Brocard J, Mortreux A (1994) Tetrahedron Lett 35:4995.

    Article  CAS  Google Scholar 

  20. Andersson Y, Långström B (1994) J Chem Soc Perkin Trans 1 1395.

    Article  Google Scholar 

  21. Uemura M, Nishimura H, Kamikawa K, Nakayama K, Hayashi Y (1994) Tetrahedron Lett 35:1909.

    Article  CAS  Google Scholar 

  22. Uemura M, Nishimura H, Hayashi T (1994) J Organomet Chem 473:129.

    Article  CAS  Google Scholar 

  23. Cald-irola P, Chowdhury R, Johansson AM, Hacksell U (1995) Organometallics 14:3897.

    Article  CAS  Google Scholar 

  24. Kiji J (1996) Macromol Symp 105:167

    CAS  Google Scholar 

  25. Illuminati G (1964) Adv Heterocycl Chem 3:285.

    Article  CAS  Google Scholar 

  26. Oae S, Furukawa N (1989) Adv Het-erocycl Chem 48:1.

    Article  Google Scholar 

  27. Zoltewicz JA, Cruskie, Jr MP, Dill CD (1995) J Org Chem 60:264

    Article  CAS  Google Scholar 

  28. Krespan CG (1995) In:Hudlický M, Pavlath AE (eds) Chemistry of organic fluorine compounds II. ACS, Washington DC, p 297

    Google Scholar 

  29. Lunin VV, Lokteva ES (1996) Russ Chem Bull 45:1519

    Article  Google Scholar 

  30. Dehmlow EV, Dehmlow SS (1983) Phase transfer catalysis. Verlag Chemie, Weinheim

    Google Scholar 

  31. Bekkevol S, Svorstoel I, Hoeiland H, Songstad J (1983) Acta Chem Scand B 37:935.

    Article  Google Scholar 

  32. Fanning JC, Keefer LK (1987) J Chem Soc Chem Commun 955. Grushin VV (1998) Angew Chem Int Ed Engl 37:994

    Google Scholar 

  33. Zefirov NS, Makhon’kov DA (1982) Chem Rev 82:615

    Article  CAS  Google Scholar 

  34. Tsuji J (1995) Palladium reagents and catalysis:innovations in organic synthesis. Wiley, Chichester

    Google Scholar 

  35. Reetz MT, Wanninger K, Hermes M (1997) Chem Commun 535.

    Google Scholar 

  36. Voigt Schik U, Meyer FE, de Meijere A (1994) Synlett 189.

    Google Scholar 

  37. Horino H, Inone N, Asao T (1981) Tetrahedron Lett 22:741

    Google Scholar 

  38. Rossi R, Carpita A, Bellina F (1995) Org Prep Proc Int 27:129

    Article  Google Scholar 

  39. Ciriano MA, Tena MA, Oro LA (1992) J Chem Soc Dalton Trans 2123.

    Google Scholar 

  40. Tejel C, Ciriano MA, Oro LA, Tiripicchio A, Ugozzoli F (1994) Organometallics 13:4153.

    Article  CAS  Google Scholar 

  41. Kiplinger JL, Richmond TG (1996) Polyhedron 16:409.

    Article  Google Scholar 

  42. Aulwurm UR, Knoch F, Kisch H (1996) Z Naturforsch B Chem Sci (1996) 51:1555.

    CAS  Google Scholar 

  43. Crespo M, Solans X, Font-Bardia M (1996) J Organomet Chem 518:105.

    Article  CAS  Google Scholar 

  44. Crespo M, Grande C, Klein A, Font-Bardia M, Solans X (1998) J Organomet Chem 563:179.

    Article  CAS  Google Scholar 

  45. Santra BK, Lahiri GK (1998) J Chem Soc Dalton Trans 1613

    Google Scholar 

  46. Portnoy M, Ben-David Y, Milstein D (1995) J Organomet Chem 503:149.

    Article  CAS  Google Scholar 

  47. Baar CR, Hill GS, Vittal JJ, Puddephatt RJ (1998) Organometallics 17:32

    Article  CAS  Google Scholar 

  48. Haarman HF, Ernsting JM, Kranenburg M, Kooijman H, Veldman N, Spek AL, van Leeuwen PWNM, Vrieze K (1997) Organometallics 16:887.

    Article  CAS  Google Scholar 

  49. Le Bras J, Amouri H, Vaissermann J (1997) J Organomet Chem 548:305

    Article  CAS  Google Scholar 

  50. 21. (a) Rondon D, He X-D, Chaudret B (1992) J Organomet Chem 433:C18.

    Article  CAS  Google Scholar 

  51. Rondon D, Delbeau J, He X-D, Sabo-Etienne S, Chaudret B (1994) J Chem Soc Dalton Trans 1895

    Google Scholar 

  52. Peng T-S, Winter CH, Gladysz JA (1994) Inorg Chem 33:2534

    Article  CAS  Google Scholar 

  53. Caubère P (1991) Rev Heteroatom Chem 4:78

    Google Scholar 

  54. Kunishima M, Hioki K, Kono K, Sakuma T, Tani S (1994) Chem Pharm Bull 42:2190

    CAS  Google Scholar 

  55. Semmelhack MF, Helquist PM, Jones LD (1971) J Am Chem Soc 93:5908.

    Article  CAS  Google Scholar 

  56. Wen-schuh E, Zimmering R (1987) Z Chem 27:448

    Article  CAS  Google Scholar 

  57. Cassar L, Foà M (1973) J Organomet Chem 51:381

    Article  CAS  Google Scholar 

  58. Gerlach DH, Kane AR, Parshall GW, Jesson JP, Muetterties EL (1971) J Am Chem Soc 93:3543

    Article  Google Scholar 

  59. Morvillo A, Turco A (1981) J Organomet Chem 208:103

    Article  CAS  Google Scholar 

  60. Fahey DR (1970) J Am Chem Soc 92:402

    Article  CAS  Google Scholar 

  61. Fahey DR, Mahan JE (1977) J Am Chem Soc 99:2501

    Article  CAS  Google Scholar 

  62. Hidai M, Kashiwagi T, Ikeuchi T, Uchida Y (1971) J Organomet Chem 30:279

    Article  CAS  Google Scholar 

  63. Fóa M, Cassar L (1975) J Chem Soc Dalton Trans 2572

    Google Scholar 

  64. Tsou TT, Kochi JK (1979) J Am Chem Soc 101:6319

    Article  CAS  Google Scholar 

  65. Osborn JA (1975) In: Ishii Y, Tsutsui M (eds) Prospects in organotransition-metal chemistry. Plenum Press, New York, p 65

    Google Scholar 

  66. Portnoy M, Milstein D (1993) Organometallics 12:1665

    Article  CAS  Google Scholar 

  67. Kalinin VN (1992) Synthesis 413

    Google Scholar 

  68. de Meijere A, Meyer F (1994) Angew Chem Int Ed Engl 33:2379

    Article  Google Scholar 

  69. Cabri W, Caudiani I (1995) Acc Chem Res 28:2

    Article  CAS  Google Scholar 

  70. Tsuji J, Mandai T (1995) Angew Chem Int Ed Engl 34:2589

    Article  CAS  Google Scholar 

  71. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  72. Percec V, Hill HH (1996) ACS Symp Ser 624:2

    CAS  Google Scholar 

  73. Beletskaya IP, Cheprakov AV (1998) In:Grieco PA (ed) Organic synthesis in water. Blackie Academic & Professional, London, p 141.

    Google Scholar 

  74. Beletskaya IP (1997) Pure Appl Chem 69:471

    Article  CAS  Google Scholar 

  75. Coulson DR (1968) J Chem Soc Chem Commun 1530

    Google Scholar 

  76. Fitton P, Rick EA (1971) J Organomet Chem 28:287

    Article  CAS  Google Scholar 

  77. Garrou PE, Heck RF (1976) J Am Chem Soc 98:4115

    Article  CAS  Google Scholar 

  78. Fauvarque J-F, Pflüger F, Troupel M (1981) J Organomet Chem 208:419

    Article  CAS  Google Scholar 

  79. Caspar JV (1985) J Am Chem Soc 107:6718

    Article  CAS  Google Scholar 

  80. Amatore C, Pflüger F (1990) Organometallics 9:2276

    Article  CAS  Google Scholar 

  81. Amatore C, Azzabi M, Jutand A (1991) J Am Chem Soc 113:8375

    Article  CAS  Google Scholar 

  82. Amatore C, Jutand A, Khalil F, M’Barki MA, Mottier L (1993) Organometallics 12:3168

    Article  CAS  Google Scholar 

  83. Amatore C, Jutand A, Suarez A (1993) J Am Chem Soc 115:9531

    Article  CAS  Google Scholar 

  84. Grushin VV, Alper H (1993) Organometallics 12:3846.

    Article  CAS  Google Scholar 

  85. Wallow TI, Goodson FE, Novak BM (1996) Organometallics 15:3708

    Article  CAS  Google Scholar 

  86. Amatore C, Carré E, Jutand A, Tanaka H, Ren Q, Torii S (1997) Chem Eur J 2:957

    Google Scholar 

  87. Herrmann WA, Broßmer C, Priermeier T, Öfele K (1994) J Organomet Chem 481:97

    Article  CAS  Google Scholar 

  88. Kong K-C, Cheng C-H (1991) J Am Chem Soc 113:6313.

    Article  CAS  Google Scholar 

  89. Goodson FE, Wallow TI, Novak BM (1997) J Am Chem Soc 119:12441 and references cited therein

    Article  CAS  Google Scholar 

  90. Amatore Jutand A (1988) Organometallics 7:2203.

    Article  Google Scholar 

  91. Amatore C, Jutand A (1990) Acta Chem Scand 44:755

    Article  CAS  Google Scholar 

  92. Amatore C, Jutand A, Khalil F, Nielsen MF (1992) J Am Chem Soc 114:7076

    Article  CAS  Google Scholar 

  93. Parshall GW (1974) J Am Chem Soc 96:2360

    Article  CAS  Google Scholar 

  94. Huser M, Youinou M-T, Osborn JA (1989) Angew Chem Int Ed Engl 28:1386

    Article  Google Scholar 

  95. Grushin VV, Alper H (1993) Organometallics 12:1890

    Article  CAS  Google Scholar 

  96. Grushin VV, Alper H (1995) J Am Chem Soc 117:4305

    Article  CAS  Google Scholar 

  97. Portnoy M, Milstein D (1993) Organometallics 12:1655

    Article  CAS  Google Scholar 

  98. Pan Y, Mague T, Fink MJ (1993) J Am Chem Soc 115:3842

    Article  CAS  Google Scholar 

  99. Widenhoefer RA, Zhong HA, Buchwald SL (1996) Organometallics 15:2745

    Article  CAS  Google Scholar 

  100. Harvey PD, Provencher R, Gagnon J, Zhang T, Fortin D, Hierso K, Drouin M, Socol SM (1996) Can J Chem 74:2268

    Article  CAS  Google Scholar 

  101. Caubère P (1983) Angew Chem Int Ed Engl 22:599

    Article  Google Scholar 

  102. Caubère P (1985) Pure Appl Chem 57:1875

    Article  Google Scholar 

  103. Brunet J-J, Sidot C, Loubinoux B, Caubère P (1979) J Org Chem 44:2199

    Article  CAS  Google Scholar 

  104. Brunet J-J, Sidot C, Caubère P (1983) J Org Chem 48:1166

    Article  CAS  Google Scholar 

  105. Foà M, Francalanci F (1987) J Mol Catal 41:89

    Article  Google Scholar 

  106. Pilloni G, Valcher S, Martelli M (1972) J Electroanal Chem 40:63

    Article  CAS  Google Scholar 

  107. Zecchin S, Schiavon G, Pilloni G, Martelli M (1976) J Organomet Chem 110:C45

    Article  CAS  Google Scholar 

  108. Love CJ, McQuillin FJ (1973) J Chem Soc Perkin Trans 1 2509

    Article  Google Scholar 

  109. Navazio G, Sandrini PL, Troilo G (1977) Atti Ist Veneto Sci Lett Arti C1 Sci Mat Nat 135:67; Chem Abstr 90:87639v

    CAS  Google Scholar 

  110. Baker RT (1994) US Patent 5,300,712; Chem Abstr 121:56984 h.

    Google Scholar 

  111. Baker RT (1994) US Patent 5,326,914; Chem Abstr 123:55371 k

    Google Scholar 

  112. Cho O-J, Lee I-M, Park K-Y, Kim H-S (1995) J Fluorine Chem 71:107.

    Article  CAS  Google Scholar 

  113. Kim_H-S, Cho O-J, Lee I-M, Hong S-P, Kwag C-Y, Ahn B-S (1996) J Mol Catal A 111:49

    Article  CAS  Google Scholar 

  114. Grushin VV, Alper H (1991) Organometallics 10:1620

    Article  CAS  Google Scholar 

  115. Grushin VV (1993) Acc Chem Res 26:279

    Article  CAS  Google Scholar 

  116. Grushin VV, Vymenits AB, Vol'pin ME (1990) J Organomet Chem 382:185

    Article  CAS  Google Scholar 

  117. Gusev DG, Bakhmutov VI, Grushin VV, Vol'pin ME (1990) Inorg Chim Acta 175:19

    Article  CAS  Google Scholar 

  118. Gusev DG, Bakhmutov VI, Grushin VV, Vol'pin ME (1990) Inorg Chim Acta 177:115

    Article  CAS  Google Scholar 

  119. Albinati A, Bakhmutov VI, Caulton KG, Clot E, Eckert J, Eisenstein Gusev DG, Grushin VV, Hauger BE, Klooster W, Koetzle TF, McMullan RK, O’Loughlin TJ, Pelissier M, Ricci JS, Sigalas MP, Vymenits AB (1993) J Am Chem Soc 115:7300

    Article  CAS  Google Scholar 

  120. Grushin VV, Vymenits AB, Vol'pin ME (1990) Metalloorg Khim 3:702.

    CAS  Google Scholar 

  121. Young RJ Jr, Grushin VV (1999) Organometallics 18:294

    Article  CAS  Google Scholar 

  122. Grushin VV, Gusev DG (1989) unpublished observations

    Google Scholar 

  123. Goryunov LI, Shteingarts VD (1991) Zh Org Khim 27:1144

    CAS  Google Scholar 

  124. Goryunov LI, Shteingarts VD (1993) Zh Org Khim 29:2230

    CAS  Google Scholar 

  125. Pinder AR (1980) Synthesis 425

    Google Scholar 

  126. Bosin TR, Raymond MG, Buckpitt AR (1973) Tetrahedron Lett 14:797

    Article  Google Scholar 

  127. Surrey AR, Hammer HF (1946) J Am Chem Soc 68:1244.

    Article  CAS  Google Scholar 

  128. Huffman JW (1959) J Org Chem 24:1759.

    Article  CAS  Google Scholar 

  129. Newman MS, Powell WH (1969) J Org Chem 34:3923.

    Article  Google Scholar 

  130. Fox BA, Threlfall (1973) Org Synth 5:346

    Google Scholar 

  131. Imai H, Nishiguchi M, Tanaka M, Fukuzumi K (1977) Chem Lett 855.

    Google Scholar 

  132. Imai H, Nishiguchi M, Tanaka M, Fukuzumi K (1977) J Org Chem 42:2309

    Article  CAS  Google Scholar 

  133. Guillaumet G, Mordenti L, Caubére P (1975) J Organomet Chem 92:43.

    Article  CAS  Google Scholar 

  134. Carfagna C, Musco A, Pontellini R, Terzoni G (1989) J Mol Catal 54:L23.

    Article  CAS  Google Scholar 

  135. Carfagna C, Musco A, Pontellini R, Terzoni G (1989) J Mol Catal 57:23.

    Article  CAS  Google Scholar 

  136. Davydov DV, Beletskaya IP (1993) Metalloorg Khim 6:111.

    CAS  Google Scholar 

  137. Davydov DV, Beletskaya IP (1993) Russ Chem Bull 42:575.

    Article  Google Scholar 

  138. Včelák J, Hetfleiš J (1994) Collect Czech Chem Commun 59:1645.

    Article  Google Scholar 

  139. Li H, Liao S, Xu Y (1996) Chem Lett 1059.

    Google Scholar 

  140. Boukherroub R, Chatgilialoglu C, Manuel G (1996) Organometallics 15:1508

    Article  CAS  Google Scholar 

  141. Qian C, Zhu D, Gu Y (1990) J Mol Catal 63:L1.

    Article  CAS  Google Scholar 

  142. Qian C, Zhu D, Gu Y (1991) J Organomet Chem 401:23.

    Article  CAS  Google Scholar 

  143. Deng DL, Qian CT, Penn JH (1994) Chin Chem Lett 5:303; Chem Abstr 121:116732 m.

    CAS  Google Scholar 

  144. Penn JH, Deng DL, Chang TQ (1996) Chin Chem Lett 7:845; Chem Abstr 125:275307a

    CAS  Google Scholar 

  145. Zhang Y, Liao S, Xu Y (1994) Tetrahedron Lett 35:4599

    Article  CAS  Google Scholar 

  146. Kang R, Yu H (1998) Huanjing Huaxue 17:159; Chem Abstr 129:148680

    CAS  Google Scholar 

  147. Wiener H, Blum J, Sasson Y (1991) J Org Chem 56:6145.

    Article  CAS  Google Scholar 

  148. Pews RG, Hunter JE, Wehmeyer RM (1993) Tetrahedron 49:4809.

    Article  CAS  Google Scholar 

  149. Balko EN, Przybylski E, Von Trentini F (1993) Appl Catal B 2:pp1.

    Article  CAS  Google Scholar 

  150. Marques CA, Selva M, Tundo P (1993) J Chem Soc Perkin Trans 1 529.

    Article  Google Scholar 

  151. Marques CA, Selva M, Tundo P (1993) J Org Chem 58:5256.

    Article  CAS  Google Scholar 

  152. Marques CA, Selva M, Tundo P (1994) J Org Chem 59:3830.

    Article  CAS  Google Scholar 

  153. Marques CA, Selva M, Tundo P (1995) J Org Chem 60:2430.

    Article  CAS  Google Scholar 

  154. Marques CA, Rogozhnikova O, Selva M, Tundo P (1995) J Mol Catal A 96:301.

    Article  CAS  Google Scholar 

  155. Sakra T, Kacetl L, Skoloudova A (1995) Chem Prum 45:118; Chem Abstr 123:313446p.

    CAS  Google Scholar 

  156. Rajagopal S, Spatola AF (1995) J Org Chem 60:1347.

    Article  CAS  Google Scholar 

  157. Simagina VI, Litvak VV, Stoyanova IV, Yakovlev VA, Mastikhin VM, Afanasenkova IV, Likholobov VA (1996) Izv Akad Nauk Ser Khim 1391

    Google Scholar 

  158. Sakai M, Lee M-S, Yamaguchi K, Kawai Y, Sasaki Sakakibara Y (1992) Bull Chem Soc Jpn 65:1739.

    Article  CAS  Google Scholar 

  159. Birke P, Herda WR, Heubner U, Koppe J, Neumann U, Schoedel R (1995) Ger DE 4, 320,462

    Google Scholar 

  160. Yanilkin VV, Maksimyuk NI, Kargin YuM (1994) Russ Chem Bull 43:957

    Article  Google Scholar 

  161. Stiles M (1994) J Org Chem 59:5381.

    Article  CAS  Google Scholar 

  162. Scrivanti A, Vicentini B, Beghetto V, Chessa G, Matteoli U (1998) Inorg Chem Commun 1:246

    Article  CAS  Google Scholar 

  163. Huser M, Osborn JA (1990) Eur Pat Appl EP 352,164; Chem Abstr 113:39527d

    Google Scholar 

  164. Ferrughelli DT, Horváth IT (1992) J Chem Soc Chem Commun 806

    Google Scholar 

  165. Bényei AC, Lehel S, Joó F (1977) J Mol Catal A 116:349

    Article  Google Scholar 

  166. Akita Y, Ohta A (1981) Heterocycles 16:1325

    Article  CAS  Google Scholar 

  167. Ben-David Y, Gozin M, Portnoy M, Milstein D (1992) J Mol Catal 73:173

    Article  CAS  Google Scholar 

  168. Amatore C, Jutand A, M’Barki MA (1992) Organometallics 11:3009.

    Article  CAS  Google Scholar 

  169. Ozawa F, Kubo A, Hayashi T (1992) Chem Lett 2177.

    Google Scholar 

  170. Mandai T, Matsumoto T, Tsuji J, Saito S (1993) Tetrahedron Lett 34:2513.

    Article  CAS  Google Scholar 

  171. Amatore C, Carré E, Jutand A, M’Barki MA (1995) Organometallics 14:1818

    Article  CAS  Google Scholar 

  172. Grushin VV, Bensimon Alper H (1995) Organometallics 14:3259

    Article  CAS  Google Scholar 

  173. Grushin VV (1996) Chem Rev 96:2011

    Article  CAS  Google Scholar 

  174. Heck RF (1979) Acc Chem Res 12:146.

    Article  CAS  Google Scholar 

  175. Heck RF (1982) Org React 27:345.

    CAS  Google Scholar 

  176. Heck RF (1985) Palladium reagents in organic synthesis. Academic Press, New York

    Google Scholar 

  177. Heck RF (1991) Vinyl substitutions with organopalladium intermediates. In:Trost BM, Flemming I (eds) Comprehensive organic synthesis. Pergamon Press, Oxford, vol 4, chap 4.3, p 833

    Google Scholar 

  178. Herrmann WA, Brossmer C, Öfele K, Reisinger C-P, Priermeier T, Beller M, Fischer H (1995) Angew Chem Int Ed Engl 34:1844.

    Article  CAS  Google Scholar 

  179. Beller M, Riermeier TH, Haber S, Kleiner H-J, Herrmann WA (1996) Chem Ber 129:1259.

    Article  CAS  Google Scholar 

  180. Herrmann WA, Brossmer C, Reisinger C-P, Priermeier T, Öfele Beller M (1997) Chem Eur J 3:1357

    Article  CAS  Google Scholar 

  181. Ohff M, Ohff A, van der Boom ME, Milstein D (1997) J Am Chem Soc 119:11687

    Article  CAS  Google Scholar 

  182. Herrmann WA, Elison M, Fischer J, Köcher Artus GRJ (1995) Angew Chem Int Ed Engl 34:2371

    Article  CAS  Google Scholar 

  183. Reetz MT, Breinbauer R, Wanninger K (1996) Tetrahedron Lett 37:4499

    Article  CAS  Google Scholar 

  184. Reetz MT, Lohmer G (1996) Chem Commun 1921

    Google Scholar 

  185. Voigt Schik U, Meyer FE, de Meijere A (1994) Synlett 189

    Google Scholar 

  186. Reardon P, Metts S, Crittendon C, Daugherity P, Parsons EJ (1995) Organometallics 14:3810

    Article  CAS  Google Scholar 

  187. Davison JB, Simon NM, Sojka SA (1984) J Mol Catal 22:349

    Article  CAS  Google Scholar 

  188. Spencer A (1984) J Organomet Chem 270:115

    Article  CAS  Google Scholar 

  189. Colon I (1982) U.S. Patent 4,334,081; Chem Abstr 97:72052u

    Google Scholar 

  190. Boldrini GP, Savoia D, Tagliavini E, Trombini C, Umani Ronchi A (1986) J Organomet Chem 301:C62

    Article  CAS  Google Scholar 

  191. Lebedev SA, Pedchenko VV, Lopatina VS, Berestova SS, Petrov ES (1990) Zh Org Khim 26:1520; Chem Abstr 114:81104j

    CAS  Google Scholar 

  192. Mori M, Ban Y (1976) Tetrahedon Lett 1803.

    Google Scholar 

  193. Mori M, Kudo S, Ban Y (1979) J Chem Soc Perkin Trans 1 771

    Article  Google Scholar 

  194. Olivero S, Duñach E (1994) Synlett 531.

    Google Scholar 

  195. Olivero S, Clinet JC, Duñach E (1995) Tetrahedron Lett 36:4429

    Article  CAS  Google Scholar 

  196. Bozell JJ, Vogt CE (1988) J Am Chem Soc 110:2655

    Article  CAS  Google Scholar 

  197. Mitra J, Mitra AK (1997) J Indian Chem Soc 74:146; Chem Abstr 126:250966

    CAS  Google Scholar 

  198. Ben-David Y, Portnoy M, Gozin M, Milstein D (1992) Organometallics 11:1995

    Article  CAS  Google Scholar 

  199. Milstein D, Ben David Y (1993) PCT Int Appl WO 9301, 173; Chem Abstr 118:254539 t

    Google Scholar 

  200. Portnoy M, Ben-David Y, Milstein D (1993) Organometallics 12:4734

    Article  CAS  Google Scholar 

  201. Herrmann WA, Broßmer Öfele Beller M, Fischer H (1995) J Mol Catal A 103:133.

    Article  CAS  Google Scholar 

  202. Herrmann WA, Broßmer Öfele Beller M, Fischer H (1995) J Organomet Chem 491:C1

    Article  CAS  Google Scholar 

  203. Portnoy M, Ben-David Y, Rousso I, Milstein D (1994) Organometallics 13:3465

    Article  CAS  Google Scholar 

  204. Dieck HA, Heck RF (1974) J Am Chem Soc 96:1133

    Article  CAS  Google Scholar 

  205. Colquhoun HM, Thompson DJ, Twigg MV (1991) Carbonylation. Direct synthesis of carbonyl compounds. Plenum Press, New York

    Google Scholar 

  206. Falbe J (1980) New synthesis with carbon monoxide. Springer, Berlin

    Google Scholar 

  207. Parshall GW, Ittel SD (1992) Homogeneous catalysis. The applications and chemistry of catalysis by soluble transition metal complexes. John Wiley and Sons, New York

    Google Scholar 

  208. Weissermel K, Arpe H-J (1997) Industrial organic chemistry, 3rd edn. VCH, New York

    Google Scholar 

  209. Foà M, Francalanci F, Bencini E, Gardano A (1985) J Organomet Chem 285:293

    Article  Google Scholar 

  210. Foà M, Francalanci F (1986) J Organomet Chem 301:C27

    Article  Google Scholar 

  211. Zhesko TE, Boyarskii VP, Beletskaya IP (1989) Metalloorg Khim 2:385; Chem Abstr 111:214202b

    CAS  Google Scholar 

  212. Cassar L Foà M, Gardano A (1976) J Organomet Chem 121:C55

    Article  Google Scholar 

  213. Cassar L (1980) Ann NY Acad Sci 333:208

    Article  CAS  Google Scholar 

  214. Sudo K, Nakasa K, Kudo M, Yamamoto M (1988) Eur Pat Appl EP 283, 194; Chem Abstr 110:172884x

    Google Scholar 

  215. Sudo Kudo M, Yamamoto M (1988) Jpn Kokai Tokkyo Koho JP 63, 227,547 [88,227,547]; Chem Abstr 111:57304 s.

    Google Scholar 

  216. Sudo K, Kudo M, Yamamoto M (1988) Eur Pat Appl EP 282,266; Chem Abstr 111:133974c

    Google Scholar 

  217. Milstein D (1991) US Pat 5,034,534; Chem Abstr 116:6544r

    Google Scholar 

  218. Perry RJ, Wilson BD (1996) J Org Chem 61:7482

    Article  CAS  Google Scholar 

  219. Kashimura T, Kudo K, Mori S, Sugita N (1986) Chem Lett 299

    Google Scholar 

  220. Kashimura T, Kudo K, Mori S, Sugita N (1986) Chem Lett 483

    Google Scholar 

  221. Kashimura T, Kudo K, Mori S, Sugita N (1986) Chem Lett 851

    Google Scholar 

  222. Kudo K, Shibata T, Kashimura T, Mori S, Sugita N (1987) Chem Lett 577

    Google Scholar 

  223. Dufaud V, Thivolle-Cazat J, Basset J-M (1990) J Chem Soc Chem Commun 426

    Google Scholar 

  224. Ben-David Y, Portnoy M, Milstein D (1989) J Am Chem Soc 111:8742

    Article  CAS  Google Scholar 

  225. Ben-David Y, Portnoy M, Milstein D (1989) J Chem Soc Chem Commun 1816

    Google Scholar 

  226. Milstein D, Ben-David Y (1991) Eur Pat Appl EP 406,848; Chem Abstr 115:135677q

    Google Scholar 

  227. Huser M, Osborn JA (1990) Eur Pat Appl EP 352,167; Chem Abstr 113:40170p

    Google Scholar 

  228. Huser M, Osborn JA (1990) Eur Pat Appl EP 352,166; Chem Abstr 113:58687x

    Google Scholar 

  229. Huser M, Metz F, Osborn JA (1990) Fr Demande FR 2, 637,281; Chem Abstr 113:152035e

    Google Scholar 

  230. Huser M, Metz F, Osborn JA (1990) Fr Demande FR 2, 637,283; Chem Abstr 114:121757h

    Google Scholar 

  231. Drent E (1993) Brit UK Pat Appl GB 2, 261,662; Chem Abstr 119:159881 k

    Google Scholar 

  232. Grushin VV, Alper H (1992) J Chem Soc Chem Commun 611

    Google Scholar 

  233. Jenner G, Ben Taleb A (1994) J Organomet Chem 470:257

    Article  CAS  Google Scholar 

  234. Miyawaki T, Nomura Hazama M, Suzukamo G (1997) J Mol Catal A 120:L9.

    Article  CAS  Google Scholar 

  235. Nomuro K, Miyawaki T (1996) Jpn Kokai Tokkyo Koho JP 08, 104,661 [96,104,661]; Chem Abstr 125:86311 m

    Google Scholar 

  236. Corain B, Favevo G (1975) J Chem Soc Dalton Trans 283

    Google Scholar 

  237. Ozawa F, Kawasaki N, Okamoto H, Yamamoto T, Yamamoto A (1987) Organometallics 6:1640

    Article  CAS  Google Scholar 

  238. Moser WR, Wang AW, Kildahl NK (1988) J Am Chem Soc 110:2816

    Article  CAS  Google Scholar 

  239. Ozawa F, Soyama H, Yanagihara H, Aoyama I, Takino H, Izawa K, Yamamoto T, Yamamoto A (1985) J Am Chem Soc 107:3235

    Article  CAS  Google Scholar 

  240. Caulton KG (1994) New J Chem 18:25

    CAS  Google Scholar 

  241. Flemming JP, Pilon MC, Borbulevitch OYa, Antipin MYu, Grushin VV (1998) Inorg Chim Acta 280:87.

    Article  CAS  Google Scholar 

  242. Amatore C, Carré E, Jutand A (1998) Acta Chem Scand 52:100

    Article  CAS  Google Scholar 

  243. Portnoy M, Frolow F, Milstein D (1991) Organometallics 10:3960.

    Article  CAS  Google Scholar 

  244. Portnoy M, Milstein D (1994) Organometallics 13:600

    Article  CAS  Google Scholar 

  245. Colon I, Kelsey DR (1986) J Org Chem 51:2627.

    Article  CAS  Google Scholar 

  246. Colon I, Maresca LM, Kwiatkowaski GT (1981) US Patent 4,263,466

    Google Scholar 

  247. Colon I (1982) J Org Chem 47:2622

    Article  CAS  Google Scholar 

  248. Iyoda M, Otsuka H, Sato Nisato N, Oda M (1990) Bull Chem Soc Jpn 63:80

    Article  CAS  Google Scholar 

  249. Rollin Y, Troupel M, Tuck DG, Perichon J (1986) J Organomet Chem 303:131.

    Article  CAS  Google Scholar 

  250. Mabrouk S, Pelligrini S, Folest JC, Rollin Y, Perichon J (1986) J Organomet Chem 301:391.

    Article  CAS  Google Scholar 

  251. Meyer G, Rollin Y, Perichon J (1987) J Organomet Chem (1987) 333:263.

    Article  CAS  Google Scholar 

  252. Meyer G, Troupel M, Perichon J (1990) J Organomet Chem 393:137

    Article  CAS  Google Scholar 

  253. Yamamoto T, Wakabayashi S, Osakada K (1992) J Organomet Chem 428:223

    Article  CAS  Google Scholar 

  254. Bochmann M, Creaser CS, Wallage L (1990) J Mol Catal 60:344.

    Google Scholar 

  255. Ikoma Y, Taya F, Ozaki E-i, Higuchi S, Naoi Y, Fuji-i K (1990) Synthesis 147.

    Google Scholar 

  256. 170. (c)Qiu Lan Z (1993) Lanzhou Daxue Xuebao, Ziran Kexueban 29:176; Chem Abstr 122:55649m.

    Google Scholar 

  257. Poetsch E, Meyer V (1995) Ger Offen DE 4, 326,169; Chem Abstr 122:239312c.

    Google Scholar 

  258. Lan Z (1996) Huaxue Shiji 18:11; Chem Abstr 125:58005w.

    CAS  Google Scholar 

  259. Ikoma Y, Naoi Y, Otani M, Ando K, Akiyama T, Sugimori A (1997) Nippon Kagaku Kaishi 119; Chem Abstr 126:250937

    Google Scholar 

  260. Fauvarque JF, Jutand A (1979) J Organomet Chem 177:273.

    Article  CAS  Google Scholar 

  261. Lebedev SA, Sorokina RS, Berestova SS, Petrov ES (1986) Izv Akad Nauk SSSR Ser Khim 679; Chem Abstr 106:84760r

    Google Scholar 

  262. Mitchell MB, Wallbank PJ (1991) Tetrahedron Lett 32:2273.

    Article  CAS  Google Scholar 

  263. Ali NM, McKillop A, Mitchell MB, Rebelo RA, Wallbank PJ (1992) Tetrahedron 48:8117.

    Article  CAS  Google Scholar 

  264. Alcock NW, Brown JM, Hulmes DI (1993) Tetrahedron: Asymmetry 4:743.

    Article  CAS  Google Scholar 

  265. Achab S, Guyot M, Potier P (1993) Tetrahedron Lett 34:2127.

    Article  CAS  Google Scholar 

  266. Janietz D, Bauer M (1993) Synthesis 33.

    Google Scholar 

  267. Beller M, Fischer H, Herrmann WA, Öfele Brossmer C (1995) Angew Chem Int Ed Engl 34:1848.

    Article  CAS  Google Scholar 

  268. Shen W (1997) Tetrahedron Lett 38:5575

    Article  CAS  Google Scholar 

  269. Saito S, Sakai M, Miyaura N (1996) Tetrahedron Lett 37:2993.

    Article  CAS  Google Scholar 

  270. Saito S, Oh-tani S, Miyaura N (1997) J Org Chem 62:8024.

    Article  CAS  Google Scholar 

  271. Indolese AF (1997) Tetrahedron Lett 38:3513

    Article  CAS  Google Scholar 

  272. Percec V, Bae J-Y, Hill DH (1995) J Org Chem 60:1060

    Article  CAS  Google Scholar 

  273. Bumagin NA, Bykov VV (1996) Russ J Gen Chem 66:1925.

    Google Scholar 

  274. Bykov VV, Bumagin NA, Beletskaya IP (1995) Doklady Chem 340:52.

    Google Scholar 

  275. Bumagin NA, Bykov VV (1997) Tetrahedron 53:14437

    Article  CAS  Google Scholar 

  276. Shirakawa E, Yamasaka K, Hiyama T (1997) J Chem Soc Perkin Trans 1 2449

    Article  Google Scholar 

  277. Gouda K-i, Hagiwara E, Hatanaka Y, Hiyama T (1996) J Org Chem 61:7232.

    Article  CAS  Google Scholar 

  278. Hagiwara E, Gouda K-i, Hatanaka Y, Hiyama T (1997) Tetrahedron Lett 38:439

    Article  CAS  Google Scholar 

  279. Cristau H-J, Desmurs J-R, Ratton S, Rignol S, Taillefer M (1996) Ind Chem Libr 8:90

    Article  CAS  Google Scholar 

  280. Keegstra MA, Brandsma L (1991) Rec Trav Chim Pays-Bas 110:299.

    CAS  Google Scholar 

  281. Keegstra MA, Peters THA, Brandsma L (1992) Tetrahedron 48:3633

    Article  CAS  Google Scholar 

  282. Muganlinskii FF, Sandler OL, Kakhramanov VB, Guseinova DD (1990) Zh Prikl Khim 63:914.

    CAS  Google Scholar 

  283. Shankaraiah B (1991) Indian Patent 167,934; Chem Abstr 116:214136m

    Google Scholar 

  284. Kawahara S (1995) Jpn Kokai Tokkyo Koho JP 07, 330,688 [95,330,688]; Chem Abstr 124:288966u.

    Google Scholar 

  285. Kawahara S (1995) Jpn Kokai Tokkyo Koho JP 07, 330,689 [95,330,689]; Chem Abstr 124:288967v

    Google Scholar 

  286. Ellis GP, Romney-Alexander TM (1987) Chem Rev 87:779

    Article  CAS  Google Scholar 

  287. Cassar L (1973) J Organomet Chem 54:C57

    Article  CAS  Google Scholar 

  288. Cassar L, Ferrara S, Foà M (1974) Adv Chem Ser 132:252

    Article  CAS  Google Scholar 

  289. Cassar L, Foà M, Montanari F, Marinelli GP (1979) J Organomet Chem 173:335

    Article  CAS  Google Scholar 

  290. Sakakibara Y, Okuda F, Shimobayashi A, Kirino K, Sakai M, Uchino N, Takagi K (1988) Bull Chem Soc Jpn 61:1985

    Article  CAS  Google Scholar 

  291. Funabiki T, Nakamura H, Yoshida S (1983) J Organomet Chem 243:95

    Article  CAS  Google Scholar 

  292. Takagi K, Sasaki K, Sakakibara Y (1991) Bull Chem Soc Jpn 64:1118 and references cited therein

    Article  CAS  Google Scholar 

  293. Akita Y, Shimazaki M (1981) Synthesis 974

    Google Scholar 

  294. Harris JF (1973) US Patent 3,755,409; Chem Abstr 79:104970p

    Google Scholar 

  295. Foà M, Santi R, Garavagila F (1981) J Organomet Chem 206:C29

    Article  Google Scholar 

  296. Cristau HJ, Chabaud B, Chêne A, Christol H (1981) Synthesis 892

    Google Scholar 

  297. Takagi K (1987) Chem Lett 2221

    Google Scholar 

  298. Takagi K (1978) Chem Lett 191

    Google Scholar 

  299. Tsou TT, Kochi JK (1980) J Org Chem 45:1930

    Article  CAS  Google Scholar 

  300. Cramer R, Coulson DR (1975) J Org Chem 40:2267.

    Article  CAS  Google Scholar 

  301. Coulson DR (1975) US Patent 3,914,311; Chem Abstr 84:43584v

    Google Scholar 

  302. Wolfe JP, Buchwald SL (1997) J Am Chem Soc 119:6054

    Article  CAS  Google Scholar 

  303. Cassar L, Foà M (1974) J Organomet Chem 74:75

    Article  CAS  Google Scholar 

  304. Allen DW, Nowell IW, March LA (1982) Tetrahedron Lett 5479

    Google Scholar 

  305. Krasil'nikova EA, Sentemov VV, Gavrilova EL (1993) Zh Obshch Khim 63:848

    Google Scholar 

  306. Reddy NP, Tanaka M (1997) Tetrahedron Lett 38:4807

    Article  CAS  Google Scholar 

  307. Nishiyama M, Yamamoto T, Koie Y (1997) 72nd Spring annual meeting of the Chemical Society of Japan. Tokyo, Japan. Abstract 2PA052.

    Google Scholar 

  308. Yamamoto T, Nishiyama M, Koie Y (1997) 72nd Spring annual meeting of the Chemical Society of Japan. Tokyo, Japan. Abstract 2PA053.

    Google Scholar 

  309. Nishiyama M, Koie Y (1997) Eur Pat Appl EP 802, 173; Chem Abstr 127:346419 t

    Google Scholar 

  310. Goryunov LI, Shteingarts VD (1995) Zh Org Khim 31:472

    CAS  Google Scholar 

  311. Poignant G, Sinbandhit S, Toupet L, Guerchais V (1998) Angew Chem Int Ed Engl 37:963

    Article  CAS  Google Scholar 

  312. Leiva C, Sutton D (1998) Organometallics 17:4568

    Article  CAS  Google Scholar 

  313. Reetz MT, Lohmer G, Schwickardi R (1998) Angew Chem Int Ed Engl 37:481

    Article  CAS  Google Scholar 

  314. Riermeier TH, Zapf A, Beller M (1997) Top Cata l 4:301.

    Article  Google Scholar 

  315. Beller M, Zapf A (1998) Synlett 793

    Google Scholar 

  316. Funabiki T, Yamazaki T, Fukui A, Tanaka T, Yoshida S (1998) Angew Chem Int Ed Engl 37:513

    Article  CAS  Google Scholar 

  317. Luo F-H, Chu C-I, Cheng C-H (1998) Organometallics 17:1025

    Article  CAS  Google Scholar 

  318. Mehnert CP, Weaver DW, Ying JY (1998) J Am Chem Soc 120:12289

    Article  CAS  Google Scholar 

  319. Yamamoto T, Nishiyama S, Koie Y (1997) Jpn Kokai Tokkyo Koho JP 10, 310,561 [97,119,477]; Chem Abstr 130:52227.

    Google Scholar 

  320. Yamamoto T, Nishiyama M, Koie Y (1998) Tetrahedron Lett 39:2367.

    Article  CAS  Google Scholar 

  321. Nishiyama M, Yamamoto T, Koie Y (1998) Tetrahedron Lett 39:617

    Article  CAS  Google Scholar 

  322. Firooznia F, Gude C, Chan Satoh Y (1998) Tetrahedron Lett 39:3985.

    Article  CAS  Google Scholar 

  323. Shen W (1997) 38:5575

    Google Scholar 

  324. Hamann Hartwig JF (1998) J Am Chem Soc 120:7369,12706

    Article  Google Scholar 

  325. Old DW, Wolfe JP, Buchwald SL (1998) J Am Chem Soc 120:9722

    Article  CAS  Google Scholar 

  326. Littke AF, Fu GC (1998) Angew Chem Int Ed Engl 37:3387.

    Article  CAS  Google Scholar 

  327. Littke AF, Fu GC (1999) J Org Chem 64:10

    Article  CAS  Google Scholar 

  328. Brenner E, Fort Y (1998) Tetrahedron Lett 39:5359

    Article  CAS  Google Scholar 

  329. Tsubomura T, Ishikura A, Hoshino K, Narita H, Sakai K (1997) Chem Lett 1171

    Google Scholar 

  330. Noskov YuG, Petrov ES (1998) React Kinet Catal Lett 64:359

    Article  CAS  Google Scholar 

  331. Reyne F, Waegell B, Brun, P (1995) Bull Chem Soc Jpn 68:1162

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Du Pont de Nemours and Company Inc., Central Research and Development, Experimental Station, Wilmington, DE, 19880-0328, USA

    Vladimir V. Grushin

  2. Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada

    Howard Alper

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  1. Vladimir V. Grushin
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  1. Department of Applied Chemistry Faculty of Engineering, Osaka University, Yamadaoka 2-1, Suita shi, Osaka, 565-0817

    Shinji Murai

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Grushin, V.V., Alper, H. (1999). Activation of Otherwise Unreactive C-Cl Bonds. In: Murai, S., et al. Activation of Unreactive Bonds and Organic Synthesis. Topics in Organometallic Chemistry, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-68525-1_8

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