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Recent Developments in Metal-Catalyzed Additions of Oxygen Nucleophiles to Alkenes and Alkynes

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 31))

Abstract

Progress in the field of metal-catalyzed redox-neutral additions of oxygen nucleophiles (water, alcohols, carboxylic acids, and others) to alkenes, alkynes, and allenes between 2001 and 2009 is critically reviewed. Major advances in reaction chemistry include development of chiral Lewis acid catalyzed asymmetric oxa-Michael additions and Lewis-acid catalyzed hydro-alkoxylations of nonactivated olefins, as well as further development of Markovnikov-selective cationic gold complex-catalyzed additions of alcohols or water to alkynes and allenes.

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Abbreviations

AZARYPHOS:

aza-aryl-phosphanes

BHT:

2,6-di-tert-butyl-4-methylphenol

BINAP:

2,2′-bis-diphenylphosphino-1,1′-binaphthyl

BINOL:

2,2′-dihydroxy-1,1′-binaphthyl

cod:

(Z,Z)-1,5-cyclooctadiene

DMAP:

4-(dimethylamino)-pyridine

dppb:

1,4-bis-(diphenylphosphino)butane

dppe:

1,2-bis-(diphenylphosphino)ethane

dppm:

1,1-bis-(diphenylphosphino)methane

IPr:

1,3-bis-(2,6-diisopropylphenyl)imidazolylidene

MOM:

methoxymethyl

MVK:

methyl vinyl ketone

TMEDA:

N,N,N′,N′-tetramethyl-ethane-1,2-diamine

TolBINAP:

2,2′-bis-(di-{4-methylphenyl})phosphino-1,1′-binaphthyl

Tf:

trifluoromethanesulfonyl

TPPH:

tetraphenylporphyrine

p-Ts:

(or: Ts) para-toluenesulfonyl

References

  1. Togni A, Grützmacher H (2001) Catalytic Heterofunctionalization. Wiley, Weinheim

    Book  Google Scholar 

  2. Burns NZ, Baran PS, Hoffmann RW (2009) Angew Chem Int Ed 48:2854

    Article  CAS  Google Scholar 

  3. Tani K, Kataoka Y (2001) In: Togni A, Grützmacher H (eds) Catalytic Heterofunctionalization. Wiley-VCH, Weinheim, p 171

    Google Scholar 

  4. Beller M, Seayad J, Tillack A, Jiao H (2004) Angew Chem Int Ed 43:3368

    Article  CAS  Google Scholar 

  5. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079

    Article  CAS  Google Scholar 

  6. Hintermann L, Labonne A (2007) Synthesis 1121

    Google Scholar 

  7. Nising CF, Bräse S (2008) Chem Soc Rev 1218

    Google Scholar 

  8. Hintermann L (2004) In: Beller M, Bolm C (eds) Transition Metals for Organic Synthesis, Vol 2, 2nd edn. Wiley-VCH, Weinheim, p 379

    Google Scholar 

  9. Henry PM (2002) In: Negishi E (ed) Handbook of Organopalladium Chemistry for Organic Synthesis, vol II. Wiley-Intersicence, New York, p 2119

    Chapter  Google Scholar 

  10. Woerpel KA, Bergman RG (1993) J Am Chem Soc 115:7888

    Article  CAS  Google Scholar 

  11. Hahn C (2004) Chem Eur J 10:5888

    Article  CAS  Google Scholar 

  12. Barone CR, Cini R, Clot E, Eisenstein O, Maresca L, Natile G, Tamasi G (2008) J Organomet Chem 693:2819

    Article  CAS  Google Scholar 

  13. Tye JW, Hartwig JF (2009) J Am Chem Soc 131:14703

    Article  CAS  Google Scholar 

  14. Bennett BL, Birnbaum J, Roddick DM (1995) Polyhedron 14:187

    Article  CAS  Google Scholar 

  15. Feducia JA, Campbell AN, Anthis JW, Gagné MR (2006) Organometallics 25:3114

    Article  CAS  Google Scholar 

  16. Parks JM, Guo H, Momany C, Liang L, Miller SM, Summers AO, Smith JC (2009) J Am Chem Soc 131:13278

    Article  CAS  Google Scholar 

  17. Koh JH, Gagné MR (2004) Angew Chem Int Ed 43:3459

    Article  CAS  Google Scholar 

  18. Qian H, Widenhoefer RA (2003) J Am Chem Soc 125:2056

    Article  CAS  Google Scholar 

  19. Liu C, Bender CF, Han X, Widenhoefer RA (2007) Chem Commun 3607

    Google Scholar 

  20. Cochran BM, Michael FE (2008) J Am Chem Soc 130:2786

    Article  CAS  Google Scholar 

  21. McKeon JE, Fitton P, Griswold AA (1972) Tetrahedron 28:227

    Article  CAS  Google Scholar 

  22. McKeon JE, Fitton P (1972) Tetrahedron 28:233

    Article  CAS  Google Scholar 

  23. Wang YG, Wu XX, Jiang ZY (2004) Tetrahedron Lett 45:2973

    Article  CAS  Google Scholar 

  24. Ozerov OV (2009) Chem Soc Rev 38:83

    Article  CAS  Google Scholar 

  25. Sanford MS, Groves JT (2004) Angew Chem Int Ed 43:588

    Article  CAS  Google Scholar 

  26. Lin YS, Takeda S, Matsumoto K (1999) Organometallics 18:4897

    Article  CAS  Google Scholar 

  27. Ochiai M, Lin YS, Yamada J, Misawa H, Arai S, Matsumoto K (2004) J Am Chem Soc 126:2536

    Article  CAS  Google Scholar 

  28. Jensen CM, Trogler WC (1986) Science 233:1069

    Article  CAS  Google Scholar 

  29. Trogler WC, Jensen CM (1987) US Patent 4684751

    Google Scholar 

  30. Ramprasad D, Yue HJ, Marsella JA (1988) Inorg Chem 27:3151

    Article  CAS  Google Scholar 

  31. Trogler WC (1988) J Chem Educ 65:294

    Article  CAS  Google Scholar 

  32. Koch HF, Girard LA, Roundhill DM (1999) Polyhedron 18:2275

    Article  CAS  Google Scholar 

  33. Richard CJ, Parkins AW (2008) New J Chem 32:151

    Article  CAS  Google Scholar 

  34. Wang SQ, Zhang ZF, Chi CQ, Wu GL, Ren JG, Wang ZW, Huang MY, Jiang YY (2008) React Funct Polym 68:424

    Article  CAS  Google Scholar 

  35. Wang SQ, Wang ZW, Yang LC, Dong JL, Chi CQ, Sui DN, Wang YZ, Ren JG, Hung MY, Jiang YY (2007) J Mol Catal A 264:60

    Article  CAS  Google Scholar 

  36. Wang X, Sui DN, Huang MY, Jiang YY (2006) Polym Adv Technol 17:163

    Article  CAS  Google Scholar 

  37. Wang SQ, Wang ZW, Dong JL, Ren JG, Huang MY, Jiang YY (2004) Chin J Catal 25:339

    CAS  Google Scholar 

  38. Xue L, Zhou DJ, Tang L, Ji XF, Huang MY, Jiang YY (2004) React Funct Polym 58:117

    Article  CAS  Google Scholar 

  39. Xue L, Jia B, Tang L, Ji XF, Huang MY, Jiang YY (2004) Polym Adv Technol 15:346

    Article  CAS  Google Scholar 

  40. Jia B, Yang X, Huang MY, Jiang YY (2003) React Funct Polym 57:163

    Article  CAS  Google Scholar 

  41. Zhang X, Li YJ, Huang MY, Jiang YY (2002) Polym Adv Technol 13:305

    Article  CAS  Google Scholar 

  42. Studer M, Blaser HU (2001) J Mol Catal A 172:277

    Article  CAS  Google Scholar 

  43. Yamamoto H, Futatsugi K (2005) Angew Chem Int Ed 44:1924

    Article  CAS  Google Scholar 

  44. Hori K, Kitagawa H, Miyoshi A, Ohta T, Furukawa I (1998) Chem Lett 1083

    Google Scholar 

  45. Coulombel L, Duñach E (2004) Green Chem 6:499

    Article  CAS  Google Scholar 

  46. Ohta T, Kataoka Y, Miyoshi A, Oe Y, Furukawa I, Ito Y (2007) J Organomet Chem 692:671

    Article  CAS  Google Scholar 

  47. Oe Y, Ohta T, Ito Y (2004) Chem Commun 1620

    Google Scholar 

  48. Oe Y, Ohta T, Ito Y (2005) Synlett 179

    Google Scholar 

  49. Ito Y, Kato R, Hamashima K, Kataoka Y, Oe Y, Ohta T, Furukawa I (2007) J Organomet Chem 692:691

    Article  CAS  Google Scholar 

  50. Tschan MJL, Thomas CM, Strub H, Carpentier JF (2009) Adv Synth Catal 351:2496

    Article  CAS  Google Scholar 

  51. Coulombel L, Favier I, Duñach E (2005) Chem Commun 2286

    Google Scholar 

  52. Lemechko P, Grau F, Antoniotti S, Duñach E (2007) Tetrahedron Lett 48:5731

    Article  CAS  Google Scholar 

  53. Bienaymé H, Ancel JE, Meilland P, Simonato JP (2000) Tetrahedron Lett 42:3339

    Article  Google Scholar 

  54. Matsui M, Yamamoto H (1995) Bull Chem Soc Jpn 68:2657

    Article  CAS  Google Scholar 

  55. Matsui M, Yamamoto H (1995) Bull Chem Soc Jpn 68:2663

    Article  CAS  Google Scholar 

  56. Coulombel L, Rajzmann M, Pons JM, Olivero S, Duñach E (2006) Chem Eur J 12:6356

    Article  CAS  Google Scholar 

  57. Anderson VE, Ruszczycky MW, Harris ME (2006) Chem Rev 106:3236

    Article  CAS  Google Scholar 

  58. Marotta E, Foresti E, Marcelli T, Peri F, Righi P, Scardovi N, Rosini G (2002) Org Lett 4:4451

    Article  CAS  Google Scholar 

  59. Zhao XL, Liu L, Chen YJ, Wang D (2007) Synlett 1357

    Google Scholar 

  60. Meshram HM, Premalatha K, Rameshbabu K, Eeshwaraiah B, Yadav JS (2004) Synth Commun 34:3091

    Article  CAS  Google Scholar 

  61. Kelly BD, Allen JM, Tundel RE, Lambert TH (2009) Org Lett 11:1381

    Article  CAS  Google Scholar 

  62. Taylor JG, Whittall N, Hii KKM (2005) Chem Commun 5103

    Google Scholar 

  63. Chaminade X, Coulombel L, Olivero S, Dunach E (2006) Eur J Org Chem 3554

    Google Scholar 

  64. Yang CG, He C (2005) J Am Chem Soc 127:6966

    Article  CAS  Google Scholar 

  65. Reich NW, Yang C, Shi Z, He C (2006) Synlett 1278

    Google Scholar 

  66. Rosenfeld DC, Shekhar S, Takemiya A, Utsunomiya M, Hartwig JF (2006) Org Lett 8:4179

    Article  CAS  Google Scholar 

  67. Li Z, Zhang J, Brouwer C, Yang CG, Reich NW, He C (2006) Org Lett 8:4175

    Article  CAS  Google Scholar 

  68. Grant VH, Liu B (2005) Tetrahedron Lett 46:1237

    Article  CAS  Google Scholar 

  69. Yang CG, Reich NW, Shi Z, He C (2005) Org Lett 7:4553

    Article  CAS  Google Scholar 

  70. Qian H, Han X, Widenhoefer RA (2004) J Am Chem Soc 126:9536

    Article  CAS  Google Scholar 

  71. Komeyama K, Morimoto T, Nakayama Y, Takaki K (2007) Tetrahedron Lett 48:3259

    Article  CAS  Google Scholar 

  72. Choi JC, Kohno K, Masuda D, Yasuda H, Sakakura T (2008) Chem Commun 777

    Google Scholar 

  73. Dzudza A, Marks TJ (2009) Org Lett 11:1523

    Article  CAS  Google Scholar 

  74. Wabnitz TC, Yu JQ, Spencer JB (2004) Chem Eur J 10:484

    Article  CAS  Google Scholar 

  75. Killian DB, Hennion GF, Nieuwland JA (1936) J Am Chem Soc 58:892

    Article  CAS  Google Scholar 

  76. Starker LN, Cosulich DB (1956) US Patent 2759005

    Google Scholar 

  77. Bloomfield JJ (1962) J Org Chem 27:2742

    Article  CAS  Google Scholar 

  78. Paparizos C, Shout RS, Shaw WG (1985) US Patent 4499308-A

    Google Scholar 

  79. Hosokawa T, Shinohara T, Ooka Y, Murahashi SI (1989) Chem Lett 2001

    Google Scholar 

  80. Miller KJ, Kitagawa T, Abu-Omar MM (2001) Organometallics 20:4403

    Article  CAS  Google Scholar 

  81. Wabnitz TC, Spencer JB (2002) Tetrahedron Lett 43:3891

    Article  CAS  Google Scholar 

  82. Gaunt MJ, Spencer JB (2001) Org Lett 3:25

    Article  CAS  Google Scholar 

  83. Wabnitz TC, Spencer JB (2003) Org Lett 5:2141

    Article  CAS  Google Scholar 

  84. Wabnitz TC, Yu JQ, Spencer JB (2003) Synlett 1070

    Google Scholar 

  85. Hayashi Y, Nishimura K (2002) Chem Lett 296

    Google Scholar 

  86. Nikitin AV, Kholuiskaya SN, Rubailo VL (1997) J Chem Biochem Kinet 3:37

    CAS  Google Scholar 

  87. Jung HH, Floreancig PE (2007) J Org Chem 72:7359

    Article  CAS  Google Scholar 

  88. Jung HH, Floreancig PE (2006) Org Lett 8:1949

    Article  CAS  Google Scholar 

  89. Yi CS, Yun SY, He Z (2003) Organometallics 22:3031

    Article  CAS  Google Scholar 

  90. Farnworth MV, Cross JM, Louie J (2004) Tetrahedron Lett 45:7441

    Article  CAS  Google Scholar 

  91. Munro-Leighton C, Delp SA, Blue ED, Gunnoe TB (2007) Organometallics 26:1483

    Article  CAS  Google Scholar 

  92. Jenner G (2002) Tetrahedron 58:4311

    Article  CAS  Google Scholar 

  93. Jenner G (2001) Tetrahedron Lett 42:4807

    Article  CAS  Google Scholar 

  94. Stewart IC, Bergman RG, Toste FD (2003) J Am Chem Soc 125:8696

    Article  CAS  Google Scholar 

  95. Yoshida T, Matsuda T, Okano T, Kitani T, Otsuka S (1979) J Am Chem Soc 101:2027

    Article  CAS  Google Scholar 

  96. Vanderwal CD, Jacobsen EN (2004) J Am Chem Soc 126:14724

    Article  CAS  Google Scholar 

  97. van Lingen HL, Zhuang W, Hansen T, Rutjes FPJT, Jørgensen KA (2003) Org Biomol Chem 1:1953

    Article  CAS  Google Scholar 

  98. Wang L, Liu X, Dong Z, Fu X, Feng X (2008) Angew Chem Int Ed 47:8670

    Article  CAS  Google Scholar 

  99. van Westrenen J, Roggen RM, Hoefnagel MA, Peters JA, Kieboom APG, van Bekkum H (1990) Tetrahedron 46:5741

    Article  Google Scholar 

  100. van Westrenen J, Peters JA, Kieboom APG, van Bekkum H (1988) J Chem Soc Dalton Trans 2723

    Google Scholar 

  101. Bzhasso NA, Pyatnitskii MP (1969) Chem Abstr 71:101239

    Google Scholar 

  102. Bzhasso NA, Pyatnitskii MP (1967) Chem Abstr 68:39013

    Google Scholar 

  103. Olson MV, Taube H (1970) J Am Chem Soc 92:3236

    Article  CAS  Google Scholar 

  104. Gahan LR, Harrowfield JM, Herlt AJ, Lindoy LF, Whimp PO, Sargeson AM (1985) J Am Chem Soc 107:6231

    Article  CAS  Google Scholar 

  105. Beinert H, Kennedy MC, Stout CD (1996) Chem Rev 96:2335

    Article  CAS  Google Scholar 

  106. Lloyd SJ, Lauble H, Prasad GS, Stout CD (1999) Prot Sci 8:2655

    Article  CAS  Google Scholar 

  107. Ganguly S, Roundhill DM (1991) J Chem Soc Chem Commun 639

    Google Scholar 

  108. Ganguly S, Roudnhill DM (1993) Organometallics 12:4825

    Article  CAS  Google Scholar 

  109. Jones ND, Meessen P, Losehand U, Patrick BO, James BR (2005) Inorg Chem 44:3290

    Article  CAS  Google Scholar 

  110. Matsukawa Y, Mizukado J, Quan H, Tamura M, Sekiya A (2005) Angew Chem Int Ed 44:1128

    Article  CAS  Google Scholar 

  111. Bryndza HE, Calabrese JC, Wreford SS (1984) Organometallics 3:1603

    Article  CAS  Google Scholar 

  112. Bryndza HE (1985) Organometallics 4:406

    Article  CAS  Google Scholar 

  113. Kim JH, Kwak S, Lee JS, Vo HT, Kim CS, Kang HJ, Kim HS, Lee H (2009) Appl Catal B 89:137

    Article  CAS  Google Scholar 

  114. Natalia D, Nguyen DQ, Oh JH, Kim H, Lee H, Kim HS (2008) J Fluorine Chem 129:474

    Article  CAS  Google Scholar 

  115. Kang JE, Lee JS, Kim DS, Lee SD, Lee H, Kim HS, Cheong M (2009) J Catal 262:177

    Article  CAS  Google Scholar 

  116. Ponomarev DA, Shevchenko SM (2007) J Chem Educ 84:1725

    Article  CAS  Google Scholar 

  117. Song F, Watanabe S, Floreancig PE, Koide K (2008) J Am Chem Soc 130:16460

    Article  CAS  Google Scholar 

  118. Lee DN, Kim GJ, Kim HJ (2009) Tetrahedron Lett 50:4766

    Article  CAS  Google Scholar 

  119. Nishizawa M, Takemoto T, Sasaki I, Nakano M, Ho E, Namba K, Yamamoto H, Imagawa H (2009) Synlett 1175

    Google Scholar 

  120. Sanz S, Jones LA, Mohr F, Laguna M (2007) Organometallics 26:952

    Article  CAS  Google Scholar 

  121. Wang W, Xu B, Hammond GB (2009) J Org Chem 74:1640

    Article  CAS  Google Scholar 

  122. Leyva A, Corma A (2009) J Org Chem 74:2067

    Article  CAS  Google Scholar 

  123. Marion N, Ramón RS, Nolan SP (2009) J Am Chem Soc 131:448

    Article  CAS  Google Scholar 

  124. Wu XF, Bezier D, Darcel C (2009) Adv Synth Catal 351:367

    Article  CAS  Google Scholar 

  125. Grotjahn DB, Lev DA (2004) J Am Chem Soc 126:12232

    Article  CAS  Google Scholar 

  126. Labonne A, Kribber T, Hintermann L (2006) Org Lett 8:5853

    Article  CAS  Google Scholar 

  127. Suzuki T, Tokunaga M, Wakatsuki Y (2001) Org Lett 3:735

    Article  CAS  Google Scholar 

  128. Hintermann L, Dang TT, Labonne A, Kribber T, Xiao L, Naumov P (2009) Chem Eur J 15:7167

    Article  CAS  Google Scholar 

  129. Hintermann L, Kribber T, Labonne A, Paciok E (2009) Synlett 2412

    Google Scholar 

  130. Grotjahn DB (2008) Dalton Trans 6497

    Google Scholar 

  131. Grotjahn DB (2008) Dalton Trans 6497

    Google Scholar 

  132. Grotjahn DB, Miranda-Soto V, Kragulj EJ, Lev DA, Erdogan G, Zeng X, Cooksy AL (2008) J Am Chem Soc 130:20

    Article  CAS  Google Scholar 

  133. Grotjahn DB, Kragulj EJ, Zeinalipour-Yazdi C, Miranda-Soto V, Lev DA, Cooksy AL (2008) J Am Chem Soc 130:10860

    Article  CAS  Google Scholar 

  134. Muzart J (2005) Tetrahedron 61:5955

    Article  CAS  Google Scholar 

  135. Isono N, Lautens M (2009) Org Lett 11:1329

    Article  CAS  Google Scholar 

  136. Yu M, Skouta R, Zhou L, Jiang HF, Yao X, Li CJ (2009) J Org Chem 74:3378

    Article  CAS  Google Scholar 

  137. Harkat H, Weibel JM, Pale P (2006) Tetrahedron Lett 47:6273

    Article  CAS  Google Scholar 

  138. Harkat H, Dembelé AY, Weibel JM, Blanc A, Pale P (2009) Tetrahedron 65:1871

    Article  CAS  Google Scholar 

  139. Wolf LB, Tjen KCMF, ten Brink HT, Blaauw RH, Hiemstra H, Schoemaker HE, Rutjes FPJT (2002) Adv Synth Catal 344:70

    Article  CAS  Google Scholar 

  140. Mindt TL, Schibli R (2007) J Org Chem 72:10247

    Article  CAS  Google Scholar 

  141. Sun C, Fang Y, Li S, Zhang Y, Zhao Q, Zhu S, Li C (2009) Org Lett 11:4084

    Article  CAS  Google Scholar 

  142. Takei I, Wakebe Y, Suzuki K, Enta Y, Suzuki T, Mizobe Y, Hidai M (2003) Organometallics 22:4639

    Article  CAS  Google Scholar 

  143. Taleb A, Lahrech M, Hacini S, Thibonnet J, Parrain JL (2009) Synlett 1597

    Google Scholar 

  144. Jury JC, Swamy NK, Yazici A, Willis AC, Pyne SG (2009) J Org Chem 74:5523

    Article  CAS  Google Scholar 

  145. Yu X, Seo SY, Marks TJ (2007) J Am Chem Soc 129:7244

    Article  CAS  Google Scholar 

  146. Seo SY, Yu X, Marks TJ (2009) J Am Chem Soc 131:263

    Article  CAS  Google Scholar 

  147. Du X, Song F, Lu Y, Chen H, Liu Y (2009) Tetrahedron 65:1839

    Article  CAS  Google Scholar 

  148. Praveen C, Kiruthiga P, Perumal PT (2009) Synlett 1990

    Google Scholar 

  149. Camacho DH, Saito S, Yamamoto Y (2002) Tetrahedron Lett 43:1085

    Article  CAS  Google Scholar 

  150. McDonald FE (1999) Chem Eur J 5:3103

    Article  CAS  Google Scholar 

  151. Balthaser BR, McDonald FE (2009) Org Lett 11:4850

    Article  CAS  Google Scholar 

  152. Wipf P, Graham TH (2003) J Org Chem 68:8798

    Article  CAS  Google Scholar 

  153. Trost BM, Rhee YH (2002) J Am Chem Soc 124:2528

    Article  CAS  Google Scholar 

  154. Gabriele B, Salerno G, De Pascali F, Costa M, Chiusoli GP (2000) J Organomet Chem 593:409

    Article  Google Scholar 

  155. Hartman JW, Sperry L (2004) Tetrahedron Lett 45:3787

    Article  CAS  Google Scholar 

  156. Liu B, De Brabander JK (2006) Org Lett 8:4907

    Article  CAS  Google Scholar 

  157. Aponick A, Li CY, Palmes JA (2009) Org Lett 11:121

    Article  CAS  Google Scholar 

  158. Belting V, Krause N (2006) Org Lett 8:4489

    Article  CAS  Google Scholar 

  159. Santos LL, Ruiz VR, Sabater MJ, Corma A (2008) Tetrahedron 64:7902

    Article  CAS  Google Scholar 

  160. Antoniotti S, Genin E, Michelet V, Genet JP (2005) J Am Chem Soc 127:9976

    Article  CAS  Google Scholar 

  161. Aponick A, Li CY, Malinge J, Marques EF (2009) Org Lett 11:4624

    Article  CAS  Google Scholar 

  162. Egi M, Azechi K, Akai S (2009) Org Lett 11:5002

    Article  CAS  Google Scholar 

  163. Genin S, Antoniotti S, Michelet V, Genet JP (2005) Angew Chem Int Ed 44:4949

    Article  CAS  Google Scholar 

  164. Li M, Hua R (2008) J Org Chem 73:8658

    Article  CAS  Google Scholar 

  165. Bruneau C, Dixneuf PH (1997) Chem Commun 507

    Google Scholar 

  166. Bruneau C, Neveux M, Kabouche Z, Ruppin C, Dixneuf PH (1991) Synlett 755

    Google Scholar 

  167. Goossen LJ, Paetzold J, Koley D (2003) Chem Commun 706

    Google Scholar 

  168. Hua R, Tian X (2004) J Org Chem 69:5782

    Article  CAS  Google Scholar 

  169. Nakagawa H, Okimoto Y, Sakaguchi S, Ishii Y (2003) Tetrahedron Lett 44:103

    Article  CAS  Google Scholar 

  170. Okimoto Y, Sakaguchi S, Ishii Y (2002) J Am Chem Soc 124:1590

    Article  CAS  Google Scholar 

  171. Cui DM, Meng Q, Zheng JZ, Zhang C (2009) Chem Commun 1577

    Google Scholar 

  172. Peng AY, Ding YX (2003) J Am Chem Soc 123:15006

    Article  CAS  Google Scholar 

  173. Gulías M, Rodríguez JR, Castedo L, Mascareñas JL (2003) Org Lett 5:1975

    Article  CAS  Google Scholar 

  174. Belting V, Krause N (2009) Org Biomol Chem 7:1221

    Article  CAS  Google Scholar 

  175. Sniady A, Durham A, Morreale MS, Wheeler KA, Dembinski R (2007) Org Lett 9:1175

    Article  CAS  Google Scholar 

  176. Aschwanden P, Frantz DE, Carreira EM (2000) Org Lett 2:2331

    Article  CAS  Google Scholar 

  177. Cantagrel F, Pinet S, Gimbert Y, Chavant PY (2005) Eur J Org Chem 2694

    Google Scholar 

  178. Debledes O, Dal Zotto C, Vrancken E, Campagne JM, Retailleau P (2009) Adv Synth Catal 351:1991

    Article  CAS  Google Scholar 

  179. Diéguez-Vázquez A, Tzschucke CC, Crecente-Campo J, McGrath S, Ley SV (2009) Eur J Org Chem 1698

    Google Scholar 

  180. Zhang Z, Lee SD, Fisher AS, Widenhoefer RA (2009) Tetrahedron 65:1794

    Article  CAS  Google Scholar 

  181. Ma S (2003) Acc Chem Res 36:701

    Article  CAS  Google Scholar 

  182. Gockel B, Krause N (2006) Org Lett 8:4485

    Article  CAS  Google Scholar 

  183. Zhang Z, Liu C, Kinder RE, Han X, Qian H, Widenhoefer RA (2006) J Am Chem Soc 128:9066

    Article  CAS  Google Scholar 

  184. Zhang Z, Widenhoefer RA (2007) Angew Chem Int Ed 46:283

    Article  CAS  Google Scholar 

  185. Hamilton GL, Kang EJ, Mba M, Toste FD (2007) Science 317:496

    Article  CAS  Google Scholar 

  186. Hashmi ASK, Blanco MC, Fischer D, Bats JW (2006) Eur J Org Chem 1387

    Google Scholar 

  187. Winter C, Krause N (2009) Green Chem 11:1309

    Article  CAS  Google Scholar 

  188. Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL (2009) Chem Eur J 15:9127

    Article  CAS  Google Scholar 

  189. Yu X, Seo SY, Marks TJ (2007) J Am Chem Soc 129:7244

    Article  CAS  Google Scholar 

  190. Zhang Z, Widenhoefer RA (2008) Org Lett 10:2079

    Article  CAS  Google Scholar 

  191. Nishina N, Yamamoto Y (2008) Tetrahedron Lett 49:4908

    Article  CAS  Google Scholar 

  192. Kawamoto T, Hirabayashi S, Guo XX, Nishimura T, Hayashi T (2009) Chem Commun 3528

    Google Scholar 

  193. Dang TT, Hintermann L (2010) Unpublished work

    Google Scholar 

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  1. Department Chemie, Technische Universität München, Lichtenbergstr. 4, 85747, Garching, Germany

    Lukas Hintermann

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  1. Lukas Hintermann
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Correspondence to Lukas Hintermann .

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  1. Sackler Fac. Exact Sciences, School of Chemístry, Tel Aviv University, Tel Aviv, 69978, Israel

    Arkadi Vigalok

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Hintermann, L. (2010). Recent Developments in Metal-Catalyzed Additions of Oxygen Nucleophiles to Alkenes and Alkynes. In: Vigalok, A. (eds) C-X Bond Formation. Topics in Organometallic Chemistry, vol 31. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12073-2_6

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