Advertisement

Direct Arylation via Cleavage of Activated and Unactivated C-H Bonds

  • Masahiro Miura
  • Masakatsu Nomura
Chapter
First Online:
  • 2.3k Downloads
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 219)

Abstract

Palladium catalyzed direct coupling of aryl halides not only with various carbon nucleophiles having acidic C-H bonds, but also with aromatic and heteroaromatic compounds accompanied by cleavage of their unactivated C-H bonds, has been significantly developed in recent years. In this review the progress of these reactions as effective methods for preparing aromatic fine compounds is summarized. A brief description of related direct coupling of arenes with unsaturated compounds is also given.

Keywords

Aryl halides Arylation Palladium catalysts Carbonyl compounds Aromatic compounds 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

6 References

  1. 1.
    Tsuji J (1995) Palladium reagents and catalysts. Wiley, ChichesterGoogle Scholar
  2. 2.
    Diederich F, Stang PJ (1997) (eds) Metal-catalyzed cross-coupling reactons. Wiley-VCH, WeinheimGoogle Scholar
  3. 3.
    Wolfe JP, Wagaw S, Marcoux J-F, Buchwald SL (1998) Acc Chem Res 31:805CrossRefGoogle Scholar
  4. 4.
    Hartwig JF (1998) Acc Chem Res 31:852CrossRefGoogle Scholar
  5. 5.
    Hartwig JF (1998) Angew Chem Int Ed 37:2046CrossRefGoogle Scholar
  6. 6.
    Frost CG, Mendonça P (1998) J Chem Soc Perkin Trans 1 2615CrossRefGoogle Scholar
  7. 7.
    Carey FA, Sunderberg RJ (1981) Advanced organic chemistry, part B. 3rd edn. Plenum, New York, p 588Google Scholar
  8. 8.
    Lindley J (1984) Tetrahedron 40:1433CrossRefGoogle Scholar
  9. 9.
    Uno M, Seto K, Takahashi S (1984) J Chem Soc Chem Commun 932Google Scholar
  10. 10.
    Uno M, Seto K, Masuda M, Ueda W, Takahashi S (1985) Tetrahedron Lett 26:1553CrossRefGoogle Scholar
  11. 11.
    Uno M, Seto K, Ueda W, Masuda M, Takahashi S (1985) Synthesis 506Google Scholar
  12. 12.
    Chiofolini MA, Browne ME (1987) Tetrahedron Lett 28:171CrossRefGoogle Scholar
  13. 13.
    Chiofolini MA, Qi H-B, Browne ME (1988) J Org Chem 53:4149CrossRefGoogle Scholar
  14. 14.
    Kawatsura M, Hartwig JF (1999) J Am Chem Soc 121:1473CrossRefGoogle Scholar
  15. 15.
    Fox JM, Huang X, Chieffi A, Buchwald SL (2000) J Am Chem Soc 122:1360CrossRefGoogle Scholar
  16. 16.
    Nishiyama M, Yamamoto T, Koie Y (1998) Tetrahedron Lett 39:617CrossRefGoogle Scholar
  17. 17.
    Yamamoto T, Nishiyama M, Koie Y (1998) Tetrahedron Lett 39:2367CrossRefGoogle Scholar
  18. 18.
    Hamman BC, Hartwig JF (1998) J Am Chem Soc 120:7369CrossRefGoogle Scholar
  19. 19.
    Old DW, Wolfe JP, Buchwald SL (1998) J Am Chem Soc 120:9722CrossRefGoogle Scholar
  20. 20.
    Littke AF, Fu GC (1998) Angew Chem Int Ed 37:3387CrossRefGoogle Scholar
  21. 21.
    Wolfe GP, Singer RA, Yang BH, Buchwald SL (1999) J Am Chem Soc 121:9550CrossRefGoogle Scholar
  22. 22.
    Littke AF, Dai C, Fu GC (2000) J Am Chem Soc 122:4020CrossRefGoogle Scholar
  23. 23.
    Littke AF, Fu GC (1999) J Org Chem 64:10CrossRefGoogle Scholar
  24. 24.
    Shaughnessy KH, Kim P, Hartwig JF (1999) J Am Chem Soc 121:2123CrossRefGoogle Scholar
  25. 25.
    Littke AF, Fu GC (1999) Angew Chem Int Ed 38:2411CrossRefGoogle Scholar
  26. 26.
    Mann G, Incarvito C, Rheingold AL, Hartwig JF (1999) J Am Chem Soc 121:3224CrossRefGoogle Scholar
  27. 27.
    Aranyos A, Old DW, Kiyomori A, Wolfe JP, Sadighi JP, Buchwald SL (1999) J Am Chem Soc 121:4369CrossRefGoogle Scholar
  28. 28.
    Watanabe M, Nishiyama M, Koie Y (1999) Tetrahedron Lett 40:8837CrossRefGoogle Scholar
  29. 29.
    Grushin VV, Alper H (1994) Chem Rev 94:1047CrossRefGoogle Scholar
  30. 30.
    Grushin VV, Alper H (1999) In: Murai S (ed) Activation of unreactive bonds and organic synthesis. Springer, Berlin Heidelberg New York, p 193CrossRefGoogle Scholar
  31. 31.
    Negishi E, Copéret C, Ma S, Liou S-Y, Liu F (1996) Chem Rev 96:365CrossRefGoogle Scholar
  32. 32.
    Negishi E, Copéret C, Sugihara T, Zhang Y (1994) Tetrahedron 50:425CrossRefGoogle Scholar
  33. 33.
    Larock RC (1999) J Organomet Chem 576:111CrossRefGoogle Scholar
  34. 34.
    Larock RC, Guo L (1995) Synlett 465Google Scholar
  35. 35.
    Legros J-Y, Toffano M, Fiaud JC, Tetrahedron (1995) 51:3235CrossRefGoogle Scholar
  36. 36.
    Legros J-Y, Primault G, Toffano M, Rivière M-A, Fiaud JC (2000) Org Lett 2:433CrossRefGoogle Scholar
  37. 37.
    Suzuki H, Yi Q, Inoue J, Kusume K, Ogawa T (1987) Chem Lett 887Google Scholar
  38. 38.
    Minami T, Isonaka T, Okada Y, Ichikawa J (1993) J Org Chem 58:7009CrossRefGoogle Scholar
  39. 39.
    Okuro K, Furuune M, Miura M, Nomura M (1993) J Org Chem 58:7606CrossRefGoogle Scholar
  40. 40.
    Pivsa-Art S, Fukui Y, Miura M, Nomura M (1996) Bull Chem Soc Jpn 69:2039CrossRefGoogle Scholar
  41. 41.
    Brunner H, Schmidt P (2000) Eur J Org Chem 2119Google Scholar
  42. 42.
    Kuwajima I, Urabe H (1982) J Am Chem Soc 104:6831CrossRefGoogle Scholar
  43. 43.
    Kosugi M, Suzuki M, Hagiwara I, Goto K, Saitoh K, Migita T (1982) Chem Lett 939Google Scholar
  44. 44.
    Kosugi M, Hagiwara I, Sumiya T, Migita T (1983) Chem Commun 344Google Scholar
  45. 45.
    Kosugi M, Hagiwara I, Sumiya T, Migita T (1984) Bull Chem Soc Jpn 57:242CrossRefGoogle Scholar
  46. 46.
    Satoh T, Kawamura Y, Miura M, Nomura M (1997) Angew Chem Int Ed Engl 36:1740CrossRefGoogle Scholar
  47. 47.
    Palucki M, Buchwald SL (1997) J Am Chem Soc 119:11, 108Google Scholar
  48. 48.
    Hamann BC, Hartwig JF (1997) J Am Chem Soc 119:12, 382CrossRefGoogle Scholar
  49. 49.
    Hou D, Mas JL (1991) US Pat 4 992 591Google Scholar
  50. 50.
    Satoh T, Inoh J-I, Kawamura Y, Kawamura Y, Miura M, Nomura M (1998) Bull Chem Soc Jpn 71:2239CrossRefGoogle Scholar
  51. 51.
    Åhman J, Wolfe JP, Troutman MV, Palucki M, Buchwald SL (1998) J Am Chem Soc 120:1918CrossRefGoogle Scholar
  52. 52.
    Shaughnessy KH, Hamann BC, Hartwig JF (1998) J Org Chem 63:6546CrossRefGoogle Scholar
  53. 53.
    Grag N, Larhed M, Hallberg A (1998) J Org Chem 63:4158CrossRefGoogle Scholar
  54. 54.
    Wang D, Wu Z (1999) Chem Commun 529Google Scholar
  55. 55.
    Muratake H, Hayakawa A, Natsume M (1997) Tetrahedron Lett 38:7577CrossRefGoogle Scholar
  56. 56.
    Muratake H, Natsume M (1997) Tetrahedron Lett 38:7581CrossRefGoogle Scholar
  57. 57.
    Piers E, Marais PC (1990) J Org Chem 55:3454CrossRefGoogle Scholar
  58. 58.
    Piers E, Renaud J (1993) J Org Chem 58:11CrossRefGoogle Scholar
  59. 59.
    Muratake H, Nakai H (1999) Tetrahedron Lett 40:2355CrossRefGoogle Scholar
  60. 60.
    Quan LG, Lamrani M, Yamamoto Y (2000) J Am Chem Soc 122:4827CrossRefGoogle Scholar
  61. 61.
    Terao Y, Satoh T, Miura M, Nomura M (1999) Bull Chem Soc Jpn 72:2345CrossRefGoogle Scholar
  62. 62.
    Terao Y, Satoh T, Miura M, Nomura M (2000) Tetrahedron 56:1315CrossRefGoogle Scholar
  63. 63.
    Chen C, Lieberman DR, Larsen RD, Verhoeven TR, Reider PJ (1997) J Org Chem 62: 2676CrossRefGoogle Scholar
  64. 64.
    Terao Y, Satoh T, Miura M, Nomura M (1998) Tetrahedron Lett 39:6203CrossRefGoogle Scholar
  65. 65.
    Yamamoto Y, Hayatsu S, Yamada J (1988) J Chem Soc Chem Commun 86Google Scholar
  66. 66.
    Yamamoto Y, Hayatsu S, Yamada J (1990) J Org Chem 55:3118CrossRefGoogle Scholar
  67. 67.
    Inoh J-I, Satoh T, Pivsa-Art S, Miura M, Nomura M (1998) Tetrahedron Lett 39:4673CrossRefGoogle Scholar
  68. 68.
    Cassar L (1975) J Organomet Chem 93:253CrossRefGoogle Scholar
  69. 69.
    Heck RF (1975) J Organomet Chem 93:259CrossRefGoogle Scholar
  70. 70.
    Sonogashira K, Tohda Y, Hagihara N (1975) Tetrahedron Lett 4467Google Scholar
  71. 71.
    Sonogashira K (1997) In: Stang PJ, Diederich F (eds) Metal-catalyzed cross-coupling reactions. Wiley-VCH, Weinheim, p 203Google Scholar
  72. 72.
    Hundermark T, Littke AF, Buchwald SL, Fu GC (2000) Org Lett 2:1729CrossRefGoogle Scholar
  73. 73.
    Okuro K, Fruune M, Enna M, Miura M, Nomura M (1993) J Org Chem 58:4716CrossRefGoogle Scholar
  74. 74.
    Ellis GP, Romney-Alexander TM (1987) Chem Rev 87:779CrossRefGoogle Scholar
  75. 75.
    Okano T, Kiji J, Toyooka Y (1998) Chem Lett 425Google Scholar
  76. 76.
    Drechsler U, Hanack M (1998) Synlett 1207Google Scholar
  77. 77.
    Kubota H, Rice KC (1998) Tetrahedron Lett 39:2907CrossRefGoogle Scholar
  78. 78.
    Jin F, Confalone PN (2000) Tetrahedron Lett 41:3271CrossRefGoogle Scholar
  79. 79.
    Dyker G, Heiermann J, Miura M, Inoh J, Pivsa-Art S, Satoh T, Nomura M (2000) Chem Eur J 6:3426CrossRefGoogle Scholar
  80. 80.
    Miura M, Pivsa-Art S, Dyker G, Heiermann J, Satoh T, Nomura M (1998) Chem Commun 1889Google Scholar
  81. 81.
    Adachi C, Tsuji T, Saito S (1990) Appl Phys Lett 56:799CrossRefGoogle Scholar
  82. 82.
    Ohmori Y, Hironaka Y, Yoshida M, Tada N, Fujii A, Yoshino K (1997) Synth Metal 85: 1241CrossRefGoogle Scholar
  83. 83.
    Herrmann WA, Brossmer C, Reisinger C-P, Riermeier TH, Öffele K, Beller M (1997) Chem Eur J 3:1357CrossRefGoogle Scholar
  84. 84.
    Goodson FE, Walow TI, Novak BM (1997) J Am Chem Soc 119:12,441CrossRefGoogle Scholar
  85. 85.
    Reetz MT, Westermann E (2000) Angew Chem Int Ed 39:165CrossRefGoogle Scholar
  86. 86.
    Bringmann G, Walter R, Weirich R (1990) Angew Chem Int Ed Engl 29:977CrossRefGoogle Scholar
  87. 87.
    Bringmann G, Breuning M, Tasler S (1999) Synthesis 525Google Scholar
  88. 88.
    Ames DE, Bull D (1982) Tetrahedron 38:383CrossRefGoogle Scholar
  89. 89.
    Ames DE, Opalko A (1983) Syntheisis 234Google Scholar
  90. 90.
    Ames DE, Opalko A (1984) Tetrahedron 40:1919CrossRefGoogle Scholar
  91. 91.
    Dyker G (1997) Chem Ber/Recueil 130:1567CrossRefGoogle Scholar
  92. 92.
    González JJ, Gracía N, Gómez-Lor B, Echavarren AM (1997) J Org Chem 62:1286CrossRefGoogle Scholar
  93. 93.
    Reisch HA, Bratcher MS, Scott LT (2000) Org Lett 2:1427CrossRefGoogle Scholar
  94. 94.
    Ryabov AD (1990) Chem Rev 90:403CrossRefGoogle Scholar
  95. 95.
    Shilov E, Shul’pin GB (1997) Chem Rev 97:2879CrossRefGoogle Scholar
  96. 96.
    Larock RC, Doty MJ, Tian Q, Zenner JM (1997) J Org Chem 62:7536CrossRefGoogle Scholar
  97. 97.
    Larock RC, Tian Q (1998) J Org Chem 63:2002CrossRefGoogle Scholar
  98. 98.
    English DS, Das K, Zenner JM, Zhang W, Kraus GA, Larock RC, Petrich JW (1997) J Phys Chem A 101:3235CrossRefGoogle Scholar
  99. 99.
    Merlic CA, McInnes DM (1997) Tetrahedron Lett 38:7661CrossRefGoogle Scholar
  100. 100.
    Catellani M, Chiusoli GP (1985) J Organomet Chem 286:C13CrossRefGoogle Scholar
  101. 101.
    Dyker G, Körning J, Jones PG, Bubenitschek P (1993) Angew Chem Int Ed Engl 32:1733CrossRefGoogle Scholar
  102. 102.
    Dyker G, Körning J, Bubenitschek P, Jones PG (1997) Liebigs Ann/Recueil 203Google Scholar
  103. 103.
    Dyker G (1993) J Org Chem 58:234CrossRefGoogle Scholar
  104. 104.
    Dyker G, Kellner A (1994) Tetrahedron Lett 35:7633CrossRefGoogle Scholar
  105. 105.
    Reiser O, Weber M, de Meijere A (1989) Angew Chem Int Ed Engl 28:1037CrossRefGoogle Scholar
  106. 106.
    Albrecht K, Reiser O, Weber M, Knieriem B, de Meijere A (1994) Tetrahedron 50:383CrossRefGoogle Scholar
  107. 107.
    Catellani M, Motti E, Paterlini L, Bocelli G, Righi L (1999) J Organomet Chem 580:191CrossRefGoogle Scholar
  108. 108.
    Catellani M, Cugini F, Bocelli G (1999) J Organomet Chem 584:63CrossRefGoogle Scholar
  109. 109.
    Dyker G, Kellner A (1998) J Organomet Chem 555:141CrossRefGoogle Scholar
  110. 110.
    Pivsa-Art S, Satoh T, Miura M, Nomura M (1997) Chem Lett 823Google Scholar
  111. 111.
    Dyker G (1994) Angew Chem Int Ed Engl 33:103CrossRefGoogle Scholar
  112. 112.
    Dyker G (1992) Angew Chem Int Ed Engl 31:1023CrossRefGoogle Scholar
  113. 113.
    Dyker G (1994) Chem Ber 127:739CrossRefGoogle Scholar
  114. 114.
    Dyker G (1993) J Org Chem 58:6426CrossRefGoogle Scholar
  115. 115.
    Dyker G, Nerenz F, Siemsen P, Bubenitschek P, Jones PG (1996) Chem Ber 129:1265CrossRefGoogle Scholar
  116. 116.
    Dyker G, Siemsen P, Softmann S, Wiegand A, Dix I, Jones PG (1997) Chem Ber/Recueil 130:261CrossRefGoogle Scholar
  117. 117.
    Catellani M, Frignani F, Rangoni A (1997) Angew Chem Int Ed Engl 36:119CrossRefGoogle Scholar
  118. 118.
    Catellani M, Cugini F (1999) Tetrahedron 55:6595CrossRefGoogle Scholar
  119. 119.
    Lautens M, Piguel S (2000) Angew Chem Int Ed 39:1045CrossRefGoogle Scholar
  120. 120.
    Catellani M, Motti E, Minari M (2000) Chem Commun 157Google Scholar
  121. 121.
    Kawamura Y, Satoh T, Miura M, Nomura M (1999) Chem Lett 961Google Scholar
  122. 122.
    Hennings DD, Iwasa S, Rawl VH (1997) J Org Chem 62:2CrossRefGoogle Scholar
  123. 123.
    Kawamura Y, Satoh T, Miura M, Nomura M (1998) Chem Lett 931Google Scholar
  124. 124.
    Salah SA, Tashtoush HI (1998) Tetrahedron 54:14,157Google Scholar
  125. 125.
    Gerhartz W (1990) (ed) Ullmann’s encyclopedia, 5th edn, vol A15. VCH, Weinheim, p 359Google Scholar
  126. 126.
    Kawamura Y, Satoh T, Miura M, Nomura M (unpublished results)Google Scholar
  127. 127.
    Kohte G, Novak C, Denkel K-H, Ohmes E, Zimmermann H (1970) Angew Chem Int Ed Engl 9:520CrossRefGoogle Scholar
  128. 128.
    Gierke W, Harrer W, Kurreck H, Reusch J (1973) Tetrahedron Lett 3681Google Scholar
  129. 129.
    Satoh T, Kametani Y, Terao Y, Miura M, Nomura M (1999) Tetrahedron Lett 40:5345CrossRefGoogle Scholar
  130. 130.
    Kametani Y, Satoh T, Miura M, Nomura M (2000) Tetrahedron Lett 41:2655CrossRefGoogle Scholar
  131. 131.
    Yin J, Buchwald SL (2000) Org Lett 2:1101CrossRefGoogle Scholar
  132. 132.
    Akita Y, Itagaki Y, Takizawa S, Ohta A (1989) Chem Pharm Bull 37:1477Google Scholar
  133. 133.
    Ohta A, Akita Y, Ohkuwa T, Chiba M, Fukunaga R, Miyafuji A, Nakata T, Tani N, Aoyagi Y (1990) Heterocycles 31:1951CrossRefGoogle Scholar
  134. 134.
    Aoyagi Y, Inoue A, Koizumi I, Hashimoto R, Tokunaga K, Gohma K, Komatsu J, Sekine K, Miyafuji A, Kunoh J, Honma R, Akita Y, Ohta A (1992) Heterocycles 33:257Google Scholar
  135. 135.
    Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M (1998) Bull Chem Soc Jpn 71: 467CrossRefGoogle Scholar
  136. 136.
    Gozzi C, Lavenot L, Ilg K, Penalva V, Lemaire M (1997) Tetrahedron Lett 38:8867CrossRefGoogle Scholar
  137. 137.
    Lavenot L, Gozzi C, Ilg K, Orlova I, Penalva V, Lemaire M (1998) J Organomet Chem 567:49CrossRefGoogle Scholar
  138. 138.
    Kondo Y, Komine T, Sakamoto T (2000) Org Lett 2:3111CrossRefGoogle Scholar
  139. 139.
    Kozikowski AP, Ma D (1991) Tetrahedron Lett 28:3317CrossRefGoogle Scholar
  140. 140.
    Kuroda T, Suzuki F (1991) Tetrahedron Lett 32:6915CrossRefGoogle Scholar
  141. 141.
    Okazawa T, Satoh T, Miura M, Nomura M (unpublished results)Google Scholar
  142. 142.
    Sévignon M, Papillon J, Schulz E, Lemaire M (1999) Tetrahedron Lett 40:5873CrossRefGoogle Scholar
  143. 143.
    Satoh T, Itaya T, Miura M, Nomura M (1996) Chem Lett 823Google Scholar
  144. 144.
    Meegalla SK, Taylor NJ, Rodorigo R (1992) J Org Chem 57:2442CrossRefGoogle Scholar
  145. 145.
    Tao W, Silverberg LJ, Rheingold AL, Heck RF (1989) Organometallics 8:2550CrossRefGoogle Scholar
  146. 146.
    Larock RC, Doty MJ (1993) J Org Chem 58:4579CrossRefGoogle Scholar
  147. 147.
    Quan LG, Gevorgyan V, Yamamoto Y (1999) J Am Chem Soc 121:3545CrossRefGoogle Scholar
  148. 148.
    Gevorgyan V, Quan LG, Yamamoto Y (1999) Tetrahedron Lett 40:4089CrossRefGoogle Scholar
  149. 149.
    Fujiwara Y, Jintoku T, Takaki K (1990) CHEMTECH 636Google Scholar
  150. 150.
    Fujiwara Y, Takaki K, Taniguchi Y (1996) Synlett 591Google Scholar
  151. 151.
    Jia C, Lu W, Kitamura T, Fujiwara Y (1999) Org Lett 1:2097CrossRefGoogle Scholar
  152. 152.
    Mikami K, Hatano M, Terada M (1999) Chem Lett 55Google Scholar
  153. 153.
    Miura M, Tsuda T, Satoh T, Miura M (1997) Chem Lett 1103Google Scholar
  154. 154.
    Miura M, Tsuda T, Satoh T, Pivsa-Art S, Nomura M (1998) J Org Chem 63:5211CrossRefGoogle Scholar
  155. 155.
    Kakiuchi F, Murai S (1999) In: Murai S (ed) Activation of unreactive bonds and organic synthesis. Springer, Berlin Heidelberg New York, p 47CrossRefGoogle Scholar
  156. 156.
    Dyker G (1999) Angew Chem Int Ed 38:1698CrossRefGoogle Scholar
  157. 157.
    Guari Y, Sabo-Etienne S, Chaudret B (1999) Eur J Inorg Chem 1047Google Scholar
  158. 158.
    Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y (2000) Science 287:1992CrossRefGoogle Scholar
  159. 159.
    Jia C, Lu W, Oyamada J, Kitamura T, Matsuda K, Irie M, Fujiwara Y (2000) J Am Chem Soc 122:7252CrossRefGoogle Scholar
  160. 160.
    Lu W, Jia C, Kitamura T, Fujiwara Y (2000) Org Lett 2:2927CrossRefGoogle Scholar
  161. 161.
    Bordwell FG (1988) Acc Chem Res 21:456CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2002

Authors and Affiliations

  • Masahiro Miura
    • 1
  • Masakatsu Nomura
    • 1
  1. 1.Department of Applied Chemistry, Faculty of EngineeringOsaka UniversitySuita, OsakaJapan

Personalised recommendations

Cite chapter

Buy options