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Volume 46, Issue 2
  • ISSN: 0032-1400
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Abstract

Palladium complexes bearing N-heterocyclic nucleophilic carbenes can function as efficient and convenient mediators of C-C and C-N cross-coupling reactions. These phosphine-free systems are highly effective in coupling reactions of aryl bromides and aryl chlorides with a variety of coupling partners. Some applications of these Palladium complexes in a range of coupling reactions are described here and catalysts, conditions and results are presented.

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2002-01-01
2024-04-25
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References

  1. Tsuji J.Tsuji J.1(a), “Palladium Reagents and Catalysts”, Wiley, Chichester, 1995; (b), Synthesis, 1990, pp. 739–749 [Google Scholar]
  2. Heck R. F.Collman J. P., Hegedus L. S., Norton J. R., and Finke R. G.Trost B. M., and Verhoeven T. R.Wilkinson G., Stone F. G., and Abel E. W.2(a), “Palladium Reagents in Organic Synthesis”, Academic Press, New York, 1985; (b), , and , “Principles and applications of Organotransition metal Chemistry”, University Science Books, Mill Valley, CA, 1987; (c) and , in “Comprehensive Organometallic Chemistry”, eds. , and , Pergamon, Oxford, 1982, Vol. 8, pp. 799–938 [Google Scholar]
  3. Torssell K. G. B.Thomson R. H.3(a), “Natural Product Chemistry”, Wiley, Chichester, 1983; (b), ‘The Chemistry of Natural Products”, blackie and Son, Glasgow, 1985 [Google Scholar]
  4. Roncali J.Yamamura K., Ono S., Ogoshi H., Masuda H., and Kuroda Y.4(a), Chem. Rev., 1992, 92, 711; (b), , , and , Synlett, 1989, 18 [Google Scholar]
  5. Littke A. F., and Fu G. C.Old D. W., Wolfe J. P., and Buchwald S. L.Wotfe J. P., Singer R. A., Yang B. H., and Buchwald S. L.Bei X., Turner H., Weinberg W. H., and Guram S.Aranyos A., Old D. W., Kiyomori A., Wolfe J. P., Sadighi S. P., and Buchwald S. L.Li G. Y.Gibson S., Eastham G. R., Foster D. F., Tooze R. P., and Cole-Hamilton D. J.Pickett T. E., and Richards C. J.Furstner A., and Leitner A.Clark M. L., Cole-Hamilton D. J., and Woollins J. D.Bedford R. B., and Cazin C. S. J.Liu S.-Y., Choi M. J., and Fu G. C.Littke A. F., Dai C., and Fu G. C.5Application of bulky electron-rich phosphines to Suzuki-Miyaura coupling using aryl chlorides: (a) and , Angew. Chem., Int. Ed. Engl, 1998, 37, 3387; (b), and , J. Am. Chem. Soc., 1998, 120, 9722; (c), , and , ibid., 1999, 121, 9550; (d), , and A. , J. Org. Chem., 1999, 64, 6797; (e), , , , and , J. Am. Chem. Soc., 1999, 121, 4369; (f), Angew. Chem., Int. Ed Engl., 2001, 40, 1513; (g), , , and , Chem. Commun., 2001, 779; (h) and , Tetrahedron Lett., 2001, 42, 3767; (i) and , Synlett, 2001, 290; (j), and , J. Chem. Soc., Dalton Trans., 2001, 2721; (k) and , Chem. Commun., 2001, 1540; (I), and , ibid., 2408; (m), and , J. Am. Chem. Soc., 2000, 122, 4020 [Google Scholar]
  6. Hamann B. C., and Hartwig J. F.Littke A. F., and Fu G. C.Reetz M. T., Lohmer G., and Schwickardi R.Bei X., Guram A. S., Turner H. W., and Weinburg W. H.Bei X., Guram A. S., Tumer H. W., and Weinburg W. H.Indolese A. F.Saito S., Oh-tani S., and Miyaura N.Saito S., Sakai M., and Miyaura N.Kumada M.For examples dealing with coupling of aryl chlorides: op. cit., (Refs 5a, 5b); (n) and , J. Am. Chem. Soc., 1998, 120, 7369; (o) and , J. Org. Chem., 1999, 64, 10; (p), and , Angew. Chem., Int. Ed Engl., 1998, 37, 481; (q), , and , Tetrahedron Lett., 1999, 40, 1237; (r), , and , ibid., 3855; (s) , ibid., 1997, 38, 3513; (t), and , J. Org. Chem., 1997, 62, 8024; (u), and , Tetrahedron Lett., 199, 37, 2993; (v) For a review, see: , Pure Appl. Chem., 1980, 52, 669 [Google Scholar]
  7. Feierstein M., Doucet H., and Santelli M.Zapf A., and Beller M.Littke A. F., and Fu G. C.6Application of bulky phosphines to Heck chemistry: (a), and , J. Org. Chem., 2001, 66, 5923; (b) and , Chem. Eur. J., 2001, 7, 2908; (c) and , J. Am. Chem. Soc., 2001, 123, 6989 [Google Scholar]
  8. Itami K., Nokami T., Ishimura Y,, Mitsudo K., Kamei T., and Yoshida J.7Application of bulky phosphines to Hiyama reaction: , , , , and , J. Am. Chem. Soc., 2001, 123, 11577 [Google Scholar]
  9. Parshall G. W., and Ittel S.Pignolet L. H.8Application of phosphine ligands in homogeneous catalysis: (a) and , “Homogeneous Catalysis”, J. Wiley and Sons, New York, 1992; (b) “Homogeneous Catalysis with metal Phosphine Complexes”, ed. , Plenum, New York, 1983 [Google Scholar]
  10. Kubas G. J.Gonzales A. A., Mukerjee S. L., Chou S.-J., Zhang K., and Hoff D. J. C.Nguyen S. T., Grubbs R. H., and Ziller J. W.Fu G. C., Nguyen S. T., and Grubbs R. H.9(a), Acc. Chem. Res., 1988, 21, 120; (b), , , and , J. Am. Chem. Soc., 1988, 110, 4419; (c), and , ibid., 1993, 115, 9858; (d), and , ibid., 9856 [Google Scholar]
  11. Jafarpour L., and Nolan S. P.Wanzlick H.-W.Lappert M. F.Arduengo III A. J., and Krafczyk R.10(a) and , Adv. Organomet. Chem., 2001, 46, 181; (b), Angew. Chem., Int. Ed. Engl., 1962, 1, 75; (c), J. Organomet. Chem., 1988, 358, 185; (d), and , Chem. Z., 1998, 32, 6 [Google Scholar]
  12. Arduengo A. J., Harlow R. L., and Kline M.11 ΠΙ, and , J. Am. Chem. Soc., 1991, 113, 361 [Google Scholar]
  13. Arduengo A. J., Rasika Dias Η. V., Harlow R. L., and Kline M.12 IIΙ, , and , J. Am. Chem. Soc., 1992, 114, 5530 [Google Scholar]
  14. Loch J. A., Albrecht M., Peris E., Mata J., Faller J. W., and Crabtree R. H.Tulloch A. A. D., Danopoulos A. A., Tizzard G. J., Coles S. J., Hursthouse M. B., and Motherwell W. B.Skelton B. W., White A. H., and Williams C. G.Nielsen D. J., Cavell K. J., and Skelton B. W.McKerrecher D., Titcomb L. R., and Williams M. R. V.Magill A. M., McGuinness D. S., Cavell K. J., Britovsek G. J. P., Gibson V. C., White A. J. P., Williams D. J., White A. H., and Skelton B. W.McGuinness D. S., Cavell K. J., Skelton B. W., and White A. H.13Recent examples of the use of NHC in coupling chemistry: (a), , , , and , Organometallics, 2002, 21, 700; (b), , , , , R. S. Hay-Motherwell and , Chem. Commun., 2001, 1270; (c) Μ. V. Baker, , and , J. Chem. Soc., Dalton Trans., 2001, 111; (d), , and A. H. White, Organometallics, 2001, 20, 995; (e) S. Caddick, F. G. N. Cloke, G. K. B. Clentsmith, P. B. Hitchcock, , and , J. Organomet. Chem., 2001, 617–618, 635; (f), , , , , , , and , ibid., 546; (g), , and , Organometallics, 1999, 18, 1596 [Google Scholar]
  15. Weskamp T., Schattenmann W. C., Spiegler M., and Herrmann W. A.Scholl M., Trnka T. M., Morgan J. P., and Grubbs R. H.Tmka T. M., and Grubbs R. H.14(a), , and , Angew. Chem., Int. Ed. Engl., 1998, 37, 2490; (b), , and , Tetrahedron Lett., 1999, 40, 2674; (c) and , Acc. Chem. Res., 2001, 34, 18 [Google Scholar]
  16. Miyaura N., and Suzuki A.Suzuki A., Diederich F., and Stang P. J.Suzuki A.15Op. cit., (Refs. 5n, 5o, 5p); (a) For a review see: and , Chem. Rev., 1995, 95, 2457; (b), in “metal-Catalyzed Cross-coupling Reactions”, eds. and , Wiley-VCH, Weinheim, 1998, pp. 49-97 and references therein; (c), J. Organomet. Chem., 1999, 576, 147 [Google Scholar]
  17. Stanforth S. P.16, Tetrahedron, 1998, 54, 263 [Google Scholar]
  18. Bumagin N. A., and Bykov V. V.Early T. R., Gordon R. S., Carroll M. A., Holmes A. B., Shute R. E., and McConvey I. F.17(a)L. Botella and C. Nájera, Angew. Chem., Int. Ed. Engl., 2002, 41, 179; (b) and , Tetrahedron, 1997, 53, 14437; (c), , , , and , Chem. Commun., 2001, 1966 [Google Scholar]
  19. Huth A., Beetz I., and Schumann I.Ennis D. S., McManus J., Richardson J., Smith G. E., and Crastairs A.Miyaura N., and Suzuki A.Uenishi J., Armstrong R. W., and Kishi Y.Uemura M., Nishimura H., Minami T., and Hayashi Y.18(a), and , Tetrahedron, 1989, 45, 6679; (b), , W. Wood-Kaczmar, , and , Org. Proc. Res. Dev., 1999, 3, 248; (c) T. Oh-e, and , J. Org. Chem., 1993, 58, 2201; (d), J.-M. Beau, and , J. Am. Chem. Soc., 1987, 109, 4756; (e), , and , ibid., 1991, 113, 5402 [Google Scholar]
  20. Regitz M.Herrmann W. A., and Kocher C.Herrmann W. A., Reisinger C. P., and Spiegler M.Zhang C., Huang J., Trudell M. T., and Nolan S. P.Bohm V. P. W., Weskamp T., and Herrmann W. A.Andrus M. B., and Song C.Zhang C., and Trudell M. L.Weskamp T., and Herrmann W. A.19Op. cit., (Refs. 5i, 10d); (a), Angew. Chem., Int. Ed. Engl., 1996, 35, 725; (b) and , Angew. Chem., Int. Ed Engl., 1997, 36, 2163; (c), and , J. Organomet. Chem., 1998, 557, 93; (d), , and , J. Org. Chem., 1999, 64, 3804; (e), C. W. K. Gstöttmayr, and , J. Organomet. Chem., 2000, 595, 186; (f) and , Org. Lett., 2001, 3, 3761; (g) and , Tetrahedron Lett., 2000, 41, 595; (h), V. P. W. Bohm and , J. Organomet. Chem., 1999, 585, 348 [Google Scholar]
  21. Grasa G. A., Viciu M. S., Huang J., Zhang C., and Trudell M. L.20, , , , and S. P. Nolan, submitted for publication
  22. Tamao K.21, K. Sumitani and M. Kumada, J. Am. Chem. Soc., 1972, 94, 4374 [Google Scholar]
  23. 22R. J. P. Corriu and J. P. Masse, J. Chem. Soc., Chem. Commun., 1972, 144 [Google Scholar]
  24. Yamamura M.23, I. Moritan and S. Murahashi, J. Organomet. Chem., 1975, 91, C39 [Google Scholar]
  25. Huang J., and Nolan S. P.24 and , J. Am. Chem. Soc., 1999, 121, 9889 [Google Scholar]
  26. Smith P. J.25, “Chemistry of Tin”, blackie, New York, 1998
  27. Casado A. L., and Espinet P.26 and , J. Am. Chem. Soc., 1998, 120, 8978 [Google Scholar]
  28. Grasa G. A., and Nolan S. P.27 and , Org. Lett., 2001, 3, 119 [Google Scholar]
  29. Mowery M. E., and DeShong P.Mowery M. E., and DeShong P.Mowery M. E., and DeShong P.DeShong P.Pilcher A. S., and DeShong P.Denmark S. E., and Wu Z.Denmark S. E., and Choi J. Y.Hom K. A.Chuit C., Corriu R. J. P., Reye C., and Young J. C.Gouda K., Hagiwara E., Hatanaka Y., and Hiyama T.Hagjwara E., Gouda K., Hatanaka Y., and Hiyama T.28(a) and , Org. Lett., 1999, 1, 2137; (b) and , J. Org. Chem., 1999, 64, 1684; (c) and , ibid., 1999, 64, 3266; (d) M.-R. Brescia and , ibid., 1998, 63, 3156; (e) and , ibid., 1996, 61, 6901; (f) and , Org. Lett., 1999, 1, 1495; (g) and , J. Am. Chem. Soc., 1999, 121, 5821; (h), Chem. Rev., 1995, 95, 1317; (i), , and , ibid., 1993, 93, 1317; (j), , and , J. Org. Chem., 1996, 61, 7232; (k), , and , Tetrahedron Lett., 1997, 38, 439 [Google Scholar]
  30. Lee H. M., and Nolan S. P.29 and , Org. Lett., 2000, 2, 20.53 [Google Scholar]
  31. 30Decreased amounts of homocoupled product were obtained using 3 equiv. PhSi(OMe)3 and reducing the temperature to 600C
  32. Beletskaya I.Reetz M. T., Davies S. G., and Murahashi S.-I.Crisp G. T.Link J. T., Overman L. E., Diederich F., and Stang P. J.Link J. T., and Overman L. E.Brase S., and deMeijere A.Dieck H. A., and Heck R. F.Dieck H. A., and Heck R. F.31(a) and Α. V. Cheprakov, Chem. Rev., 2000, 100, 3009; (b), in “Transition metal Catalyzed Reactions”, eds. and , blackwell Science, Oxford, 1999; (c), Chem. Soc. Rev., 1998, 27, 427; (d) and , in “metal-Catalyzed Cross-coupling Reactions”, eds. and , Wiley-VCH, New York, 1998, pp. 231-266; (e) and , Chemtech, 1998, 28, 19; (f) and , op. cit., (Ref. d); (g) and , J. Org. Chem., 1975, 40, 1083; (h) and , J. Am. Chem. Soc., 1974, 96, 1133 [Google Scholar]
  33. Schwarz J., Bohm V. P. W., Gardiner M. G., Grosche M., Herrmann W. A., Hieringer W., and Ralldaschl-Sieber G.Tulloch A. A. D., Danopoulos A. A., Tooze R. P., Cafferkey S. M., Kleinhenz S., and Hursthouse M. B.McGuinness D. S., and Cavell K. J.Herrmann W. A., Fischer J., Elison M., Kocher C., and Artus G. R. J.Herrmann W. A., Elison M., Fischer J., Kocher C., and Artus G. R. J.32Op. cit., (Ref. 13g); (a), , , , , and , Chem. Eur. J., 2000, 6, 1773; (b), , , , and , Chem. Commun., 2000, 1274; (c) and , Organometallics, 2000, 19, 741; (d), , , and , Chem. Eur. J., 1996, 2, 772; (e), , , and , Angew. Chem., Int. Ed Engl., 1995, 34, 2371 [Google Scholar]
  34. Albert K.33, P. Gisdakis and N. Rösch, Organometallics, 1998, 17, 1608 [Google Scholar]
  35. Yang C., Lee H. M., and Nolan S. P.34, and , Org. Lett., 2001, 3, 1511 [Google Scholar]
  36. Yang C., and Nolan S. P.35 and , Synlett, 2001, 1539 [Google Scholar]
  37. Cassar L.36, J. Organomet. Chem., 1975, 93, 253 [Google Scholar]
  38. Nicolaou K. C., and Sorensen E. J.Brandsma L., Vasilevsky S. F., and Verkruijsse H. D.Rusanov A. L., and Khotina I. A.37(a) and , “Classics in Total Synthesis”, Wiley-VCH, Weinheim, 1996, pp. 582-586; (b), and , “application of Transition metal Catalysts in Organic Synthesis”, Springer-Verlag, Berlin, 1998, pp. 179-225; (c), and M. M. Begretov, Russ. Chem. Rev., 1997, 66, 10.53 [Google Scholar]
  39. Tsuji J.Sonogashira K.Rossi R., Carpita A., and Bellina F.Campbell I. B., and Taylor R. J. K.Sonogashira K., and Trost B. M.Sonogashira K., Tohda Y., and Hagihara N.38(a), op. cit., (Ref. la), pp. 168-171; (b), op. cit., (Ref. 31d), pp. 203-229; (c), and , Org. Prep. Proc. Int., 1995, 27, 127; (d), in “Organocopper Reagents”, ed. , IRL Press, Oxford, 1994, pp. 217-235; (e), in “Comprehensive Organic Synthesis”, ed. , Pergamon, New York, 1991, pp. 521-549; (f), and , Tetrahedron Lett., 1975, 4467 [Google Scholar]
  40. Bohm V. P. W., and Herrmann W. A.Hundertmark T., Littke A. F., Buchwald S. L., and Fu C. G.39(a) and , Eur. J. Org. Chem., 2000, 22, 3679; (b), , and , Org. Lett., 2000, 2, 1729 [Google Scholar]
  41. Herrmann W. A., Bohm V. P. W., Grosche M., and Weskamp T.40, , C. W. K. Gstöttmayr, , C.-P. Reisinger and , J. Organomet. Chem., 2001, 617–618, 616 [Google Scholar]
  42. McGuinness D. S., and Cavell K. J.41Op. cit., (Ref. 19d); (a) and , Organometallics, 2000, 19, 741s [Google Scholar]
  43. Wolfe J. P., and Buchwald S. L.Hartwig J. F.Hartwig J. F.Hartwig J. F.Yang B. H., and Buchwald S. L.42Recent reviews of Palladium- and nickel-mediated aryl aminations: (a), S. Wagaw, J.-F. Marcoux and , Acc. Chem. Res., 1998, 31, 80.5; (b), Acc. Chem. Res., 1998, 31, 852; (c), Angew. Chem., Int. Ed Engl., 1998, 37, 2046; (d), Synlett, 1997, 329; (e) and , J. Organomet. Chem., 1999, 576, 125 [Google Scholar]
  44. Wolfe J. P., and Buchwald S. L.Bei X., Uno T., Norris J., Turner H. W., Guram A. S., and Petersen J. L.Brenner E., and Fort Y.Yamamoto T., Nishiyama M., Kole Y., Wolfe J. P., and Buchwald S. L.Reddy N. P., and Tanaka M.Stauffer S. R., Lee S., Stambuli J. P., Hauck S. I., and Hartwig J. F.43For examples of amination of aryl chlorides, see: op. cit., (Refs. 5b, 5n, 5q); (a) and , Angew. Chem., Int. Ed, 1999, 38, 2413; (b), , , , W. H. Weinburg, and , Organometallics, 1999, 18, 1840; (c) and , Tetrahedron Lett., 1998, 39, 5359; (d), and , ibid., 2367; (e) and , J. Am. Chem. Soc., 1997, 119, 60.54; (f) T. H. Riermeir, A. Zapf and M. Beller, Top. Catal., 1997, 4301; (g) and , Tetrahedron Lett., 1997, 38, 4807; (h), , , and , Org. Lett., 2000, 2, 1423 [Google Scholar]
  45. Titcomb L. R., Caddick S., Cloke F. G. N., Wilson D. J., and McKerrecher D.44, , , and , Chem. Commun., 2001, 1388 [Google Scholar]
  46. Huang J., Grasa G. A., and Nolan S. P.45, and , Org. Lett., 1999, 1, 1307 [Google Scholar]
  47. Grasa G. A., Viciu M., Huang J., and Nolan S. P.46, , and , J. Org. Chem., 2001, 86, 7729 [Google Scholar]
  48. Paul F., Patt J., and Hartwig J. F.47, and , Organometallics, 1995, 14, 3030 [Google Scholar]
  49. Marchini P., Liso G., and Reho A.Lane C. F.48(a), and , J. Org. Chem., 1975, 40, 3453; (b), Synthesis, 1975, 135 [Google Scholar]
  50. Perregaard J., Arut J., Bogrso K. P., Hyttel J., and Sánchez C.49, , , and , J. Med Chem., 1992, 35, 1090 [Google Scholar]
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Palladium/Nucleophilic Carbene Catalysts for Cross-Coupling Reactions
Platinum Metals Review 46, 50 (2002); https://doi.org/10.1595/003214002X4625064
/content/journals/10.1595/003214002X4625064
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