Skip to content
1887
Volume 46, Issue 2
  • ISSN: 0032-1400

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.

Loading

Article metrics loading...

/content/journals/10.1595/003214002X4625064
2002-01-01
2024-11-23
Loading full text...

Full text loading...

/deliver/fulltext/pmr/46/2/pmr0046-0050.html?itemId=/content/journals/10.1595/003214002X4625064&mimeType=html&fmt=ahah

References

  1. J. Tsuji,J. Tsuji,1(a), “Palladium Reagents and Catalysts”, Wiley, Chichester, 1995; (b), Synthesis, 1990, pp. 739749 [Google Scholar]
  2. R. F. Heck,J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke,B. M. Trost, T. R. Verhoeven,G. Wilkinson, F. G. Stone, E. W. Abel,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. 799938 [Google Scholar]
  3. K. G. B. Torssell,R. H. Thomson,3(a), “Natural Product Chemistry”, Wiley, Chichester, 1983; (b), ‘The Chemistry of Natural Products”, blackie and Son, Glasgow, 1985 [Google Scholar]
  4. J. Roncali,K. Yamamura, S. Ono, H. Ogoshi, H. Masuda, Y. Kuroda,4(a), Chem. Rev., 1992, 92, 711; (b), , , and , Synlett, 1989, 18 [Google Scholar]
  5. A. F. Littke, G. C. Fu,D. W. Old, J. P. Wolfe, S. L. Buchwald,J. P. Wotfe, R. A. Singer, B. H. Yang, S. L. Buchwald,X. Bei, H. Turner, W. H. Weinberg, S. Guram,A. Aranyos, D. W. Old, A. Kiyomori, J. P. Wolfe, S. P. Sadighi, S. L. Buchwald,G. Y. Li,S. Gibson, G. R. Eastham, D. F. Foster, R. P. Tooze, D. J. Cole-Hamilton,T. E. Pickett, C. J. Richards,A. Furstner, A. Leitner,M. L. Clark, D. J. Cole-Hamilton, J. D. Woollins,R. B. Bedford, C. S. J. Cazin,S.-Y. Liu, M. J. Choi, G. C. Fu,A. F. Littke, C. Dai, G. C. Fu,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. B. C. Hamann, J. F. Hartwig,A. F. Littke, G. C. Fu,M. T. Reetz, G. Lohmer, R. Schwickardi,X. Bei, A. S. Guram, H. W. Turner, W. H. Weinburg,X. Bei, A. S. Guram, H. W. Tumer, W. H. Weinburg,A. F. Indolese,S. Saito, S. Oh-tani, N. Miyaura,S. Saito, M. Sakai, N. Miyaura,M. Kumada,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. M. Feierstein, H. Doucet, M. Santelli,A. Zapf, M. Beller,A. F. Littke, G. C. Fu,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. K. Itami, T. Nokami, Y, Ishimura, K. Mitsudo, T. Kamei, J. Yoshida,7Application of bulky phosphines to Hiyama reaction,: , , , , and , J. Am. Chem. Soc., 2001, 123, 11577 [Google Scholar]
  9. G. W. Parshall, S. Ittel,L. H. Pignolet,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. G. J. Kubas,A. A. Gonzales, S. L. Mukerjee, S.-J. Chou, K. Zhang, D. J. C. Hoff,S. T. Nguyen, R. H. Grubbs, J. W. Ziller,G. C. Fu, S. T. Nguyen, R. H. Grubbs,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. L. Jafarpour, S. P. Nolan,H.-W. Wanzlick,M. F. Lappert,A. J. Arduengo III, R. Krafczyk,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. A. J. Arduengo, R. L. Harlow, M. Kline,11 ΠΙ, and , J. Am. Chem. Soc., 1991, 113, 361 [Google Scholar]
  13. A. J. Arduengo, Η. V. Rasika Dias, R. L. Harlow, M. Kline,12 IIΙ, , and , J. Am. Chem. Soc., 1992, 114, 5530 [Google Scholar]
  14. J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree,A. A. D. Tulloch, A. A. Danopoulos, G. J. Tizzard, S. J. Coles, M. B. Hursthouse, W. B. Motherwell,B. W. Skelton, A. H. White, C. G. Williams,D. J. Nielsen, K. J. Cavell, B. W. Skelton,D. McKerrecher, L. R. Titcomb, M. R. V. Williams,A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White, B. W. Skelton,D. S. McGuinness, K. J. Cavell, B. W. Skelton, A. H. White,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. T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann,M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs,T. M. Tmka, R. H. Grubbs,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. N. Miyaura, A. Suzuki,A. Suzuki, F. Diederich, P. J. Stang,A. Suzuki,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. S. P. Stanforth,16, Tetrahedron, 1998, 54, 263 [Google Scholar]
  18. N. A. Bumagin, V. V. Bykov,T. R. Early, R. S. Gordon, M. A. Carroll, A. B. Holmes, R. E. Shute, I. F. McConvey,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. A. Huth, I. Beetz, I. Schumann,D. S. Ennis, J. McManus, J. Richardson, G. E. Smith, A. Crastairs,N. Miyaura, A. Suzuki,J. Uenishi, R. W. Armstrong, Y. Kishi,M. Uemura, H. Nishimura, T. Minami, Y. Hayashi,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. M. Regitz,W. A. Herrmann, C. Kocher,W. A. Herrmann, C. P. Reisinger, M. Spiegler,C. Zhang, J. Huang, M. T. Trudell, S. P. Nolan,V. P. W. Bohm, T. Weskamp, W. A. Herrmann,M. B. Andrus, C. Song,C. Zhang, M. L. Trudell,T. Weskamp, W. A. Herrmann,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. G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell,20, , , , and S. P. Nolan, submitted for publication
  22. K. Tamao,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. M. Yamamura,23, I. Moritan and S. Murahashi, J. Organomet. Chem., 1975, 91, C39 [Google Scholar]
  25. J. Huang, S. P. Nolan,24 and , J. Am. Chem. Soc., 1999, 121, 9889 [Google Scholar]
  26. P. J. Smith,25, “Chemistry of Tin”, blackie, New York, 1998
  27. A. L. Casado, P. Espinet,26 and , J. Am. Chem. Soc., 1998, 120, 8978 [Google Scholar]
  28. G. A. Grasa, S. P. Nolan,27 and , Org. Lett., 2001, 3, 119 [Google Scholar]
  29. M. E. Mowery, P. DeShong,M. E. Mowery, P. DeShong,M. E. Mowery, P. DeShong,P. DeShong,A. S. Pilcher, P. DeShong,S. E. Denmark, Z. Wu,S. E. Denmark, J. Y. Choi,K. A. Hom,C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young,K. Gouda, E. Hagiwara, Y. Hatanaka, T. Hiyama,E. Hagjwara, K. Gouda, Y. Hatanaka, T. Hiyama,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. H. M. Lee, S. P. Nolan,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. I. Beletskaya,M. T. Reetz, S. G. Davies, S.-I. Murahashi,G. T. Crisp,J. T. Link, L. E. Overman, F. Diederich, P. J. Stang,J. T. Link, L. E. Overman,S. Brase, A. deMeijere,H. A. Dieck, R. F. Heck,H. A. Dieck, R. F. Heck,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. J. Schwarz, V. P. W. Bohm, M. G. Gardiner, M. Grosche, W. A. Herrmann, W. Hieringer, G. Ralldaschl-Sieber,A. A. D. Tulloch, A. A. Danopoulos, R. P. Tooze, S. M. Cafferkey, S. Kleinhenz, M. B. Hursthouse,D. S. McGuinness, K. J. Cavell,W. A. Herrmann, J. Fischer, M. Elison, C. Kocher, G. R. J. Artus,W. A. Herrmann, M. Elison, J. Fischer, C. Kocher, G. R. J. Artus,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. K. Albert,33, P. Gisdakis and N. Rösch, Organometallics, 1998, 17, 1608 [Google Scholar]
  35. C. Yang, H. M. Lee, S. P. Nolan,34, and , Org. Lett., 2001, 3, 1511 [Google Scholar]
  36. C. Yang, S. P. Nolan,35 and , Synlett, 2001, 1539 [Google Scholar]
  37. L. Cassar,36, J. Organomet. Chem., 1975, 93, 253 [Google Scholar]
  38. K. C. Nicolaou, E. J. Sorensen,L. Brandsma, S. F. Vasilevsky, H. D. Verkruijsse,A. L. Rusanov, I. A. Khotina,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. J. Tsuji,K. Sonogashira,R. Rossi, A. Carpita, F. Bellina,I. B. Campbell, R. J. K. Taylor,K. Sonogashira, B. M. Trost,K. Sonogashira, Y. Tohda, N. Hagihara,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. V. P. W. Bohm, W. A. Herrmann,T. Hundertmark, A. F. Littke, S. L. Buchwald, C. G. Fu,39(a) and , Eur. J. Org. Chem., 2000, 22, 3679; (b), , and , Org. Lett., 2000, 2, 1729 [Google Scholar]
  41. W. A. Herrmann, V. P. W. Bohm, M. Grosche, T. Weskamp,40, , C. W. K. Gstöttmayr, , C.-P. Reisinger and , J. Organomet. Chem., 2001, 617–618, 616 [Google Scholar]
  42. D. S. McGuinness, K. J. Cavell,41Op. cit., (Ref. 19d); (a) and , Organometallics, 2000, 19, 741s [Google Scholar]
  43. J. P. Wolfe, S. L. Buchwald,J. F. Hartwig,J. F. Hartwig,J. F. Hartwig,B. H. Yang, S. L. Buchwald,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. J. P. Wolfe, S. L. Buchwald,X. Bei, T. Uno, J. Norris, H. W. Turner, A. S. Guram, J. L. Petersen,E. Brenner, Y. Fort,T. Yamamoto, M. Nishiyama, Y. Kole, J. P. Wolfe, S. L. Buchwald,N. P. Reddy, M. Tanaka,S. R. Stauffer, S. Lee, J. P. Stambuli, S. I. Hauck, J. F. Hartwig,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. L. R. Titcomb, S. Caddick, F. G. N. Cloke, D. J. Wilson, D. McKerrecher,44, , , and , Chem. Commun., 2001, 1388 [Google Scholar]
  46. J. Huang, G. A. Grasa, S. P. Nolan,45, and , Org. Lett., 1999, 1, 1307 [Google Scholar]
  47. G. A. Grasa, M. Viciu, J. Huang, S. P. Nolan,46, , and , J. Org. Chem., 2001, 86, 7729 [Google Scholar]
  48. F. Paul, J. Patt, J. F. Hartwig,47, and , Organometallics, 1995, 14, 3030 [Google Scholar]
  49. P. Marchini, G. Liso, A. Reho,C. F. Lane,48(a), and , J. Org. Chem., 1975, 40, 3453; (b), Synthesis, 1975, 135 [Google Scholar]
  50. J. Perregaard, J. Arut, K. P. Bogrso, J. Hyttel, C. Sánchez,49, , , and , J. Med Chem., 1992, 35, 1090 [Google Scholar]
/content/journals/10.1595/003214002X4625064
Loading
/content/journals/10.1595/003214002X4625064
Loading

Data & Media loading...

  • Article Type: Research Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test