Practical Palladium Catalysts for C-N and C-O Bond Formation

  • Alex R. Muci
  • Stephen L. Buchwald
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 219)


The development of new palladium catalysts for the arylation of amines and alcohols with aryl halides and sulfonates is reviewed. Initial systems as well as mechanistic issues are discussed briefly, while subsequent generations of catalysts are described in greater detail. For these later generations of catalysts, substrate scope and limitations are also discussed. The review is organized by substrate class. Modifications and improvements in technical aspects of reaction development are described where appropriate. In addition, applications of this technology toward natural product synthesis, new synthetic methodology, and medicinal chemistry are chronicled. This review is organized in a manner that is designed to be useful to the synthetic organic chemist.


Amination Arylation Catalyst Ligand Palladium 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

5 References

  1. 1.
    For leading references, see: Buckingham J (1994) Dictionary of Natural Products. University Press, Cambridge, MAGoogle Scholar
  2. 2.
    Czarnik AW (1996) Acc Chem Res 29:112CrossRefGoogle Scholar
  3. 3.
    For leading references, see: (a) Hornak LA (1992) (ed) Polymers for Lightwave and Integrated Optics. Marcel Dekker, New York. (b) Law K-Y (1993) Chem Rev 93:449Google Scholar
  4. 4.
    For leading references, see: (a) MacDiarmid AG (1997) Synth Met 84:27. (b) MacDiarmid AG, Chiang JC, Richter AF, Somasiri NL, Epstein AJ (1987) In: Alcacer L (ed) Conducting Polymers. Reifel, Dordrecht, The Netherlands. pp 105–120. (c) Gospodinova N, Terlemezyan L (1998) Prog Polym Sci 23:1443CrossRefGoogle Scholar
  5. 5.
    For leading references, see: (a) Melissaris AP, Litt MH (1994) Macromolecules 27:888 (b) Irvin JA, Neef CJ, Kane KM, Cassidy PE, Tullos G, St. Clair AK (1992) J Polym Sci Part A: Polym Chem 30:1675CrossRefGoogle Scholar
  6. 6.
    Larock RC (1999) Comprehensive Organic Transformations: A Guide to Functional Group Preparations. Wiley-VCH, New YorkGoogle Scholar
  7. 7.
    Smith MB, March J (2001) March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5th Edition. Wiley-Interscience, New YorkGoogle Scholar
  8. 8.
    For leading references on the Ullman etherification, see: (a) Fagan PJ, Hauptman E, Shapiro R, Casalnuovo A (2000) J Am Chem Soc 122:5043 (b) Kalinin AV, Bower JF, Riebel P, Snieckus V (1999) J Org Chem 64:2986 (c) Ragan JA, Malowski TW, Castalki MJ, Hill PD (1998) Synthesis 1599CrossRefGoogle Scholar
  9. 9.
    Wolfe JP, Wagaw S, Marcoux JF, Buchwald SL (1998) Acc Chem Res 31:805CrossRefGoogle Scholar
  10. 10.
    Hartwig JF (1998) Acc Chem Res 31:852CrossRefGoogle Scholar
  11. 11.
    For leading references, see: (a) Widenhoefer RA, Buchwald SL (1998) J Am Chem Soc 120:6504 (b) Widenhoefer RA, Zhong HA, Buchwald SL (1997) J Am Chem Soc 119:6787 (c) Zhong HA, Widenhoefer RA (1997) Inorg Chem 36:2610 (d) Alcazar-Roman LM, Hartwig JF, Rheingold AL, Liable-Sands LM, Guzei IA (2000) J Am Chem Soc 122:4618 (e) Hamann BC, Hartwig JF (1998) J Am Chem Soc 120:3694 (e) Driver MS, Hartwig JF (1997) J Am Chem Soc 119:8232 (f) Driver MS, Hartwig JF (1997) Organometallics 16:5706CrossRefGoogle Scholar
  12. 12.
    (a) Sawyer JS (2000) Tetrahedron 56:5045 (b) Hartwig JF (1999) Pure Appl Chem 71:1417 (c) Yang BH, Buchwald SL (1999) J Organomet Chem 576:125 (d) Frost CG, Mendonca P (1998) J Chem Soc-Perkin Trans. 1 2615 (e) Hartwig JF (1998) Angew Chem Int Ed 37:2047 (f) Hartwig JF (1997) Synlett 329CrossRefGoogle Scholar
  13. 13.
    For leading references on Ni-catalyzed carbon-heteroatom bond formation reactions: (a) Desmarets C, Schneider R, Fort Y (2000) Tetrahedron Lett 41:2875 (b) Brenner E, Schneider R, Fort Y (2000) Tetrahedron Lett 41:2881 (c) Mann G, Hartwig JF (1997) J Org Chem 62:5413 (d) Lipshutz BH, Ueda H (2000) Angew Chem Int Ed 39:4492 (e) Wolfe JP, Buchwald SL (1997) J Am Chem Soc 119:6054 Copper-catalyzed C-N bond formation: (f) Collman JP, Zhong M (2000) Org Lett 2:1233CrossRefGoogle Scholar
  14. 14.
    (a) Kosugi M, Kameyama M, Sano H, Migita T (1983) Chem Lett 927 (b) Kosugi M, Kameyama M, Sano H, Migita T (1985) Nippon Kagaku Kaishi 547Google Scholar
  15. 15.
    (a) Boger, DL, Panek JS (1984) Tetrahedron Lett 25:3175 (b) Boger, DL, Duff, SR, Panek JS, Yasuda M (1985) J Org Chem 50:5782 (c) Boger DL, Duff SR, Panek JS, Yasuda M (1985) J Org Chem 50:5790CrossRefGoogle Scholar
  16. 16.
    Guram AS, Buchwald SL (1994) J Am Chem Soc 116:7901CrossRefGoogle Scholar
  17. 17.
    Guram AS, Rennels RA, Buchwald SL (1995) Angew Chem Int Ed Eng 34:1348CrossRefGoogle Scholar
  18. 18.
    Louie J, Hartwig JF (1995) Tetrahedron Lett 36:3609CrossRefGoogle Scholar
  19. 19.
    Mann G, Hartwig JF (1996) J Am Chem Soc 118:13109CrossRefGoogle Scholar
  20. 20.
    Driver MS, Hartwig JF (1995) J Am Chem Soc 117:4708CrossRefGoogle Scholar
  21. 21.
    Hartwig JF, Richards S, Barañano D, Paul F (1996) J Am Chem Soc 118:3626CrossRefGoogle Scholar
  22. 22.
    Ipaktschi J, Sharifi A (1998) Monatsh Chem 129:915Google Scholar
  23. 23.
    Kanbara T, Honma A, Hasegawa K (1996) Chem Lett 1135Google Scholar
  24. 24.
    (a) Witulski B (1999) Synlett 1223 (b) Witulski B, Zimmerman Y, Darcos V, Desvergne J-P, Bassani DM, Bouas-Laurent H (1998) Tetrahedron Lett 39:4807Google Scholar
  25. 25.
    (a) Kerrigan F, Martin C, Thomas GH (1998) Tetrahedron Lett 39:2219 (b) Zhao S-H, Miller AK, Berger J, Flippin LA (1996) Tetrahedron Lett 37:4463CrossRefGoogle Scholar
  26. 26.
    Beletskaya IP, Bessmertnykh AG, Mishechkin RA, Guilard R (1998) Rus. Chem Bull 47:1416CrossRefGoogle Scholar
  27. 27.
    (a) Wolfe JP, Buchwald SL (2000) J Org Chem 65:1144 (b) Wolfe JP, Wagaw S, Buchwald SL (1996) J Am Chem Soc 118:7215CrossRefGoogle Scholar
  28. 28.
    Racemic BINAP is commercially available from Strem Chemical CompanyGoogle Scholar
  29. 29.
    Driver MS, Hartwig JF (1996) J Am Chem Soc 118:7217CrossRefGoogle Scholar
  30. 30.
    Prashad, M, Hu, B, Lu, Y. S, Draper, R, Har, D, Repic, O, Blacklock, T. J J Org Chem 2000, 65, 2612–2614.CrossRefGoogle Scholar
  31. 31.
    Ward YD, Farina V (1996) Tetrahedron Lett 37:6993CrossRefGoogle Scholar
  32. 32.
    Willoughby CA, Chapman KT (1996) Tetrahedron Lett 37:7181CrossRefGoogle Scholar
  33. 33.
    Morita S, Kitano K, Matsubara J, Ohtani T, Kawano Y, Otsubo K, Uchida M (1998) Tetrahedron 54:4811CrossRefGoogle Scholar
  34. 34.
    Tanoury GJ, Senanayake CH, Hett R, Kuhn AM, Kessler DW, Wald SA (1998) Tetrahedron Lett 39:6845CrossRefGoogle Scholar
  35. 35.
    Kung P-P, Casper MD, Cook KL, Wilson-Lingardo L, Risen LM, Vickers TA, Ranken R, Blyn LB, Wyatt JR, Cook, PD, Ecker DJ (1999) J Med Chem 42:4705CrossRefGoogle Scholar
  36. 36.
    Nishiyama M, Yamamoto T, Koie Y (1998) Tetrahedron Lett 39:617CrossRefGoogle Scholar
  37. 37.
    Marcoux JF, Wagaw S, Buchwald SL (1997) J Org Chem 62:1568CrossRefGoogle Scholar
  38. 38.
    Hayashi T, Mise T, Fukushima M, Kagotani M, Nagashima N, Hamada Y, Matsumoto A, Kawakami S, Konishi M, Yamamoto K, Kumada M (1980) Bull Chem Soc Jpn 53:1138CrossRefGoogle Scholar
  39. 39.
    Racemic Ligand 3 is commercially available from Strem Chemical CompanyGoogle Scholar
  40. 40.
    Wolfe JP, Buchwald SL (1997) Tetrahedron Lett 38:6359CrossRefGoogle Scholar
  41. 41.
    Torisawa Y, Nishi T, Minamikawa J-I (2000) Bioorg Med Chem Lett 10:2489CrossRefGoogle Scholar
  42. 42.
    (a) Wolfe JP, Tomori H, Sadighi JP, Yin J, Buchwald SL (2000) J Org Chem 65:1158 (b) Old DW, Wolfe JP, Buchwald SL (1998) J Am Chem Soc 120:9722CrossRefGoogle Scholar
  43. 43.
    Ligand 4 is commercially available from Strem Chemical CompanyGoogle Scholar
  44. 44.
    For an account detailing the preparation of this class of ligands, see: Tomori H, Fox JM, Buchwald SL (2000) J Org Chem 65:5334CrossRefGoogle Scholar
  45. 45.
    Kranich R, Eis K, Geis O, Mühle S, Bats JW, Schmalz H-G (2000) Chem Eur J 6:2874CrossRefGoogle Scholar
  46. 46.
    Zhang X-X, Buchwald SL (2000) J Org Chem 65:8027CrossRefGoogle Scholar
  47. 47.
    Bei XH, Uno T, Norris J, Turner HW, Weinberg WH, Guram AS, Petersen JL (1999) Organometallics 18:1840CrossRefGoogle Scholar
  48. 48.
    Wolfe JP, Buchwald SL (1999) Angew Chem Int Ed 38:2413CrossRefGoogle Scholar
  49. 49.
    Ligand 6 is commercially available from Strem Chemical CompanyGoogle Scholar
  50. 50.
    Hartwig JF, Kawatsura M, Hauck SI, Shaughnessy KH, Alcazar-Roman LM (1999) J Org Chem 64:5575CrossRefGoogle Scholar
  51. 51.
    (a) For leading references, see: (a) Arduengo AJ III (1999) Acc Chem Res 32:913 (b) Arduengo AJ III; Rasika-Dias HV, Harlow RL, Kline M (1992) J Am Chem Soc 114:5530 (c) Arduengo AJ III, Rasika-Dias HV, Calabrese JC, Davidson FJ (1992) J Am Chem Soc 114:4391CrossRefGoogle Scholar
  52. 52.
    Huang J, Grasa G, Nolan SP (1999) Org Lett 1:1307CrossRefGoogle Scholar
  53. 53.
    Whitesides GM, Gaasch JF, Stedronsky ER (1972) J Am Chem Soc 94:5258CrossRefGoogle Scholar
  54. 54.
    Wagaw S, Rennels RA, Buchwald SL (1997) J Am Chem Soc 119:8451CrossRefGoogle Scholar
  55. 55.
    Marinetti A, Hubert P, Genêt J-P (2000) Eur J Org Chem 1815Google Scholar
  56. 56.
    Togni A (1990) Chimia 50:86Google Scholar
  57. 57.
    Kranenburg M, van der Burgt YEM, Kamer PC, van Leeuwan PWNM, Goubitz K, Fraanje J (1995) Organometallics 14:3081CrossRefGoogle Scholar
  58. 58.
    Harris MC, Geis O, Buchwald SL (1999) J Org Chem 64:6019CrossRefGoogle Scholar
  59. 59.
    Plante OJ, Buchwald SL, Seeberger PH (2000) J Am Chem Soc 122:7148CrossRefGoogle Scholar
  60. 60.
    Kamikawa K, Sugimoto S, Uemura M (1998) J Org Chem 63:8407CrossRefGoogle Scholar
  61. 61.
    Ogasawara M, Yoshida K, Hayashi T (2000) Organometallics 19:1567CrossRefGoogle Scholar
  62. 62.
    Buchmeiser MR, Wurst K (1999) J Am Chem Soc 121:11101CrossRefGoogle Scholar
  63. 63.
    Djakovitch L, Wagner M, Köhler K (1999) J Organometallic Chem 592:225CrossRefGoogle Scholar
  64. 64.
    (a) Louie J, Hartwig JF, Fry AJ (1997) J Am Chem Soc 119:11695 (b) Louie J, Hartwig JF (1998) Macromolecules 31:6737 (c) Goodson FE Hartwig JF (1998) Macromolecules 31:1700 (d) Goodson FE, Hauck SI, Hartwig JF (1999) J Am Chem Soc 121:7527 (e) Hauck SI, Lakshmi KV, Hartwig JF (1999) Org Lett 1:2057CrossRefGoogle Scholar
  65. 65.
    Yamamoto T, Nishiyama M, Koie Y (1998) Tetrahedron Lett 39:2367CrossRefGoogle Scholar
  66. 66.
    (a) Tew GN, Pralle MU, Stupp SI (2000) Angew Chem Int Ed 39:517 (b) Braig T, Muller DC, Gross M, Meerholz K, Nuyken O (2000) Macromol Rap Commun 21:583 (c) Thelakkhat M, Hagen J, Haarer D, Schmidt H-W (1999) Synth Met 102:1125CrossRefGoogle Scholar
  67. 67.
    Wolfe JP, Buchwald SL (1996) J Org Chem 61:1133CrossRefGoogle Scholar
  68. 68.
    Wolfe JP, Buchwald SL (1997) J Org Chem 62:6066CrossRefGoogle Scholar
  69. 69.
    Lee, S, Lee, W-M, Sulikowski, GAJ Org Chem 1999, 64, 4224CrossRefGoogle Scholar
  70. 70.
    Beller M, Riermeier TH, Reisinger C-P, Herrman WA (1997) Tetrahedron Lett 38:2073CrossRefGoogle Scholar
  71. 71.
    Reddy NP, Tanaka M (1997) Tetrahedron Lett 38:4807CrossRefGoogle Scholar
  72. 72.
    Hamann BC, Hartwig JF (1998) J Am Chem Soc 120:7369CrossRefGoogle Scholar
  73. 73.
    (a) Butler IR, Cullen WR, Kim TJ, Rettig SJ, Trotter J (1985) Organometallics 4:972 (b) Cullen WR, Kim TJ, Einstein FWB, Jones T (1983) Organometallics 4:714CrossRefGoogle Scholar
  74. 74.
    Phosphine 14 is commercially available from Strem Chemical Company.Google Scholar
  75. 75.
    Bei X, Guram AS, Turner HW, Weinberg WH (1999) Tetrahedron Lett 40:1237CrossRefGoogle Scholar
  76. 76.
    Stauffer SR, Lee SW, Stambuli JP, Hauck SI, Hartwig JF (2000) Org Lett 2:1423CrossRefGoogle Scholar
  77. 77.
    For a review on the Stille reaction, see: Mitchell TN (1998) Organotin Reagents in Cross-Coupling In: Diederich F, Stang PJ (eds) Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH, Weinheim p 167CrossRefGoogle Scholar
  78. 78.
    For a review on the Suzuki reaction, see: Suzuki A (1999) Journal of Organometallic Chemistry 576:147CrossRefGoogle Scholar
  79. 79.
    For a review on the Heck reaction, see: Beletskaya IP, Cheprakov AV (2000) Chemical Reviews 100:3009CrossRefGoogle Scholar
  80. 80.
    Wolfe JP, Buchwald SL (1997) J Org Chem 62:1264CrossRefGoogle Scholar
  81. 81.
    Louie J, Driver MS, Hamann BC, Hartwig JF (1997) J Org Chem 62:1268CrossRefGoogle Scholar
  82. 82.
    Åhman J, Buchwald SL (1997) Tetrahedron Lett 38:6363CrossRefGoogle Scholar
  83. 83.
    Demadrille R, Moustrou C, Samat A, Guglielmetti R (1999) Heterocycl Commun 5:123Google Scholar
  84. 84.
    Wentland MP, Xu G, Cioffi, CL, Ye Y, Duan W, Cohen DJ, Colasurdo AM, Bidlack JM (2000) Bioorg Med Chem Lett 10:183CrossRefGoogle Scholar
  85. 85.
    Rivas FM, Riaz U, Diver ST (2000) Tetrahedron: Asymmetry 11:1703CrossRefGoogle Scholar
  86. 86.
    Cabanal-Duvillard I, Mangeny P (1999) Tetrahedron Lett 40:3877CrossRefGoogle Scholar
  87. 87.
    Hong Y, Senanayake CH, Xiang T, Vandenbossche CP, Tanoury GJ, Bakale RP, Wald SA (1998) Tetrahedron Lett 39:3121CrossRefGoogle Scholar
  88. 88.
    (a) Beletskaya IP, Bessmertnykh AG, Mishechkin RA, Guilard R (1998) Russ Chem Bull 47:1416 (b) Beletskaya IP, Bessmertnykh AG, Guilard R (1997) Tetrahedron Lett 38:2287 (c) Beletskaya IP, Bessmertnykh AG, Guilard R (1999) Synlett 1459CrossRefGoogle Scholar
  89. 89.
    (a) Greco GE, Popa AI, Schrock RR (1998) Organometallics 17:5591 (b) Liang L-C, Schrock RR, Davis WM, McConville DH (1999) J Am Chem Soc 121:5897 (c) Schrock RR, Casado AL, Goodman JT, Liang L-C, Bonitatebus PJ, Davis WM (2000) Organometallics 19:5325CrossRefGoogle Scholar
  90. 90.
    Lim CW, Lee S-G (2000) Tetrahedron 56:5131CrossRefGoogle Scholar
  91. 91.
    Rossen K, Pye, PJ, Maliakal A, Volante RP (1997) J Org Chem 62:6462CrossRefGoogle Scholar
  92. 92.
    MacNeil SL, Gray M, Briggs LE, Li JJ; Snieckus V (1998) Synlett 419Google Scholar
  93. 93.
    Emoto T, Kubosaki N, Yamagiwa Y, Kamikawa T (2000) Tetrahedron Lett 41:355CrossRefGoogle Scholar
  94. 94.
    Kanbara T, Izumi K, Nakadani Y, Narise T, Hasegawa K (1997) Chemistry Lett 1185Google Scholar
  95. 95.
    (a) Singer RA, Sadighi JP, Buchwald SL (1998) J Am Chem Soc 120:213 (b) Sadighi JP, Singer RA, Buchwald SL (1998) J Am Chem Soc 120:4960CrossRefGoogle Scholar
  96. 96.
    Frost CG, Mendonça P (1997) Chemistry Lett 1159Google Scholar
  97. 97.
    (a) Vyskocil S, Smrcina M, Kocovsky P (1998) Tetrahedron Lett 39:9289 (b) Vyskocil S, Jaracz S, Smrcina M, Sticha M, Hanus V, Polasek M, Kocovsky P (1998) J Org Chem 63:7727CrossRefGoogle Scholar
  98. 98.
    Sadighi JP, Harris MC, Buchwald SL (1998) Tetrahedron Lett 39:5327CrossRefGoogle Scholar
  99. 99.
    Zhang X-X, Sadighi JP; Mackewitz TW, Buchwald SL (2000) J Am Chem Soc 122:7606CrossRefGoogle Scholar
  100. 100.
    Thayumanavan S, Barlow S, Marder SR (1997) Chem Mat 9:3231CrossRefGoogle Scholar
  101. 101.
    Harris MC, Buchwald SL (2000) J Org Chem 65:5327CrossRefGoogle Scholar
  102. 102.
    Denmark SE, Su X, Nishigaichi Y, Coe DM, Wong K-T, Winter SBD, Choi JY (1999) J Org Chem 64:1958CrossRefGoogle Scholar
  103. 103.
    Ohta K, Kawachi E, Inoue N, Fukasawa H, Hashimoto Y, Itai A, Kagechika H (2000) Chem Pharm Bull 48:1504Google Scholar
  104. 104.
    Imwinkelried R (1997) Chimia 51:300Google Scholar
  105. 105.
    (a) Togni A, Breutel C, Soares MC, Zanetti N, Gerfin T, Gramlich V, Spindler F, Rihs G (1994) Inorg Chim Acta 222:213 (b) Zanetti N, Spindler F, Spencer J, Togni A, Rihs G (1996) Organometallics 15:860CrossRefGoogle Scholar
  106. 106.
    Hicks FA, Brookhart M (2000) Organic Lett 2:219CrossRefGoogle Scholar
  107. 107.
    Singer RA, Buchwald SL (1999) Tetrahedron Lett 40:1095CrossRefGoogle Scholar
  108. 108.
    Wolfe JP, Ahman J, Sadighi JP, Singer RA, Buchwald SL (1997) Tetrahedron Lett 38:6367CrossRefGoogle Scholar
  109. 109.
    Mann G, Hartwig JF, Driver MS, Fernandez-Rivas C (1998)J Am Chem Soc 120:827CrossRefGoogle Scholar
  110. 110.
    Becker S, Böhm A, Müllen K (2000) Chem Eur. J 6:3984CrossRefGoogle Scholar
  111. 111.
    Purohit V, Basu AK (2000) Org Lett 2:1871CrossRefGoogle Scholar
  112. 112.
    Obst U, Betschmann P, Lerner C, Seiler P, Diederich F, Gramlich V, Weber L, Banner DW, Schönholzer P (2000) Helvetica Chimica Acta 83:855CrossRefGoogle Scholar
  113. 113.
    Deng B-L, Lepoivre JA, Lemière G (1999) Eur J Org Chem 2683Google Scholar
  114. 114.
    Jaime-Figueroa S, Liu Y, Muchowski JM, Putnam DG (1998) Tetrahedron Lett 39:1313CrossRefGoogle Scholar
  115. 115.
    Hori K, Mori M (1998) J Am Chem Soc 120:7651CrossRefGoogle Scholar
  116. 116.
    Shakespeare WC (1999) Tetrahedron Lett 40:0235CrossRefGoogle Scholar
  117. 117.
    Yin JJ, Buchwald SL (2000) Org Lett 2:1101CrossRefGoogle Scholar
  118. 118.
    Watanabe M, Nishiyama M, Yamamoto T, Koie Y (2000) Tetrahedron Lett 41:481CrossRefGoogle Scholar
  119. 119.
    Old DW, Harris MC, Buchwald SL (2000) Org Lett 2:1403CrossRefGoogle Scholar
  120. 120.
    Petrassi, HM, Klabunde T, Sacchettini J, Kelly JW (2000) J Am Chem Soc 122:2178CrossRefGoogle Scholar
  121. 121.
    (a) Wagaw S, Yang BH, Buchwald SL (1998) J Am Chem Soc 120:6621 (b) Wagaw S, Yang BH, Buchwald SL (1999) J Am Chem Soc 121:10251CrossRefGoogle Scholar
  122. 122.
    Hartwig JF (1998) Angew Chem Int Ed 37:2090CrossRefGoogle Scholar
  123. 123.
    Wang Z, Skerjl RT, Bridger GJ (1999) Tetrahedron Lett 40:3543CrossRefGoogle Scholar
  124. 124.
    (a) Bolm C, Hildebrand JP (1998) Tetrahedron Lett 39:5731 (b) Bolm, C, Hildebrand JP, Rudolph J (2000) Synthesis 911 (c) Bolm C, Hildebrand JP (2000) J Org Chem 65:169CrossRefGoogle Scholar
  125. 125.
    Harmata M, Pavri N (1999) Angew Chem Int Ed 38:2419CrossRefGoogle Scholar
  126. 126.
    Edmonson SD, Mastracchio A, Parmee ER (2000) Org Lett 2:1109CrossRefGoogle Scholar
  127. 127.
    De Riccardis F, Bonala RR, Johnson F (1999) J Am Chem Soc 121:10453CrossRefGoogle Scholar
  128. 128.
    Wagaw S, Buchwald SL (1996) J Org Chem 61:7240CrossRefGoogle Scholar
  129. 129.
    Batch A, Dodd RH (1998) J Org Chem 63:872CrossRefGoogle Scholar
  130. 130.
    Rouden J, Bernard A, Lasne M-C (1999) Tetrahedron Lett 40:8109CrossRefGoogle Scholar
  131. 131.
    Watanabe M, Yamamoto T, Nishiyama M (2000) Chem Comm 133Google Scholar
  132. 132.
    Luker TJ, Beaton HG, Whiting M, Mete A, Cheshire DR (2000) Tetrahedron Lett 41:7731CrossRefGoogle Scholar
  133. 133.
    (a) Lópes-Rodríguez ML, Viso A, Benhamú B Rominguera JL, Murcia M Bioorg Med Chem Lett (1999) 9:2339 (b) Lópes-Rodríguez ML, Benhamú, B, Ayala D, Rominguera JL, Murcia M, Ramos JA, Viso A (2000) Tetrahedron 56:3245CrossRefGoogle Scholar
  134. 134.
    Watanabe M, Yamamoto T, Nishiyama M (2000) Angew Chem Int Ed 39:2501CrossRefGoogle Scholar
  135. 135.
    Lakshman MK, Keeler JC, Hilmer JH, Martin JQ (1999) J Am Chem Soc 121:6090CrossRefGoogle Scholar
  136. 136.
    (a) Harwood EA, Sigurdsson ST, Edfeldt NBF, Reid BR, Hopkins PB (1999) J Am Chem Soc 121:5081 (b) De Riccardis F, Johnson F (2000) Org Lett 2:293CrossRefGoogle Scholar
  137. 137.
    (a) Chida N, Suzuki T, Tanaka S, Yamada I (1999) Tetrahedron Lett 40:2573 (b) Suzuki T, Tanaka S, Yamada I, Koashi Y, Yamada K, Chida N (2000) Org Lett 2:1137CrossRefGoogle Scholar
  138. 138.
    Wolfe JP, Rennels RA, Buchwald SL (1996) Tetrahedron 52:7525CrossRefGoogle Scholar
  139. 139.
    Aoki K, Peat AJ, Buchwald SL (1998) J Am Chem Soc 120:3068CrossRefGoogle Scholar
  140. 140.
    Abouabdellah A, Dodd RH (1998) Tetrahedron Lett 39:2119CrossRefGoogle Scholar
  141. 141.
    Peat AJ, Buchwald SL (1996) J Am Chem Soc 118:1028CrossRefGoogle Scholar
  142. 142.
    Wood JL, Stoltz BM, Dietrich HJ, Pflum DA, Petsch DT (1997) J Am Chem Soc 119:9641CrossRefGoogle Scholar
  143. 143.
    Yang BH, Buchwald SL (1999) Org Lett 1:35CrossRefGoogle Scholar
  144. 144.
    He F, Foxman BM, Snider BB (1998) J Am Chem Soc 120:6417CrossRefGoogle Scholar
  145. 145.
    Mann G, Hartwig JF (1996) J Am Chem Soc 118:13109CrossRefGoogle Scholar
  146. 146.
    Palucki M, Wolfe JP, Buchwald SL (1997) J Am Chem Soc 119:3395CrossRefGoogle Scholar
  147. 147.
    Watanabe M, Nishiyama M, Koie Y (1999) Tetrahedron Lett 40:8837CrossRefGoogle Scholar
  148. 148.
    Mann G, Incarvito C, Rheingold AL, Hartwig JF (1999) J Am Chem Soc 121:3224CrossRefGoogle Scholar
  149. 149.
    Shelby Q, Kataoka N, Mann G, Hartwig JF (2000) J Am Chem Soc 122:10718CrossRefGoogle Scholar
  150. 150.
    Mann G, Hartwig JF (1997) J Org Chem 62:5413CrossRefGoogle Scholar
  151. 151.
    Mann G, Hartwig JF (1997) Tetrahedron Lett 38:8005CrossRefGoogle Scholar
  152. 152.
    Aranyos A, Old DW, Kiyomor, A, Wolfe JP, Sadighi JP, Buchwald SL (1999) J Am Chem Soc 121:4369CrossRefGoogle Scholar
  153. 153.
    Palucki M, Wolfe JP, Buchwald SL (1996) J Am Chem Soc 118:10333CrossRefGoogle Scholar
  154. 154.
    Torraca KE, Kuwabe SI, Buchwald SL (2000) J Am Chem Soc 122:12907CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2002

Authors and Affiliations

  • Alex R. Muci
    • 1
  • Stephen L. Buchwald
    • 1
  1. 1.Department of ChemistryMassachusetts Institute of TechnologyCambridgeUSA

Personalised recommendations