Ruthenium- and gold-catalysed sequential reactions: A straightforward synthesis of substituted oxazoles from propargylic alcohols and amides

Chemical Communications

Volumn , Issue 23, 2004, Pages 2712-2713

  Milton, Marilyn Daisy ^a   Inada, Youichi ^a   Nishibayashi, Yoshiaki ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; OXAZOLE DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 11144304660     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411180j     Document Type: Article

References (26)

1. Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. D. Milton, M. Hidai and S. Uemura, Angew. Chem., Int. Ed, 2003, 42, 2681.
2. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
3. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
4. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
5. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
6. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
7. For recent examples: examples where two catalysts activated different functional groups in the same medium, (a) M. Sawamura, M. Sudoh and Y. Ito, J. Am. Chem. Soc., 1996, 118, 3309; (b) S. Kamijo and Y. Yamamoto, Angew. Chem., Int. Ed., 2002, 41, 3230 and references therein; examples where two different catalytic cycles proceeded in the same medium; (c) R. W. Barnhart, G. C. Bazan and T. Mourey, J. Am. Chem. Soc., 1998, 120, 1082; (d) N. Jeong, S. D. Seo and J. Y. Shin, J. Am. Chem. Soc., 2000, 122, 10220; (e) Z. J. A. Komon, G. M. Diamond, M. K. Leclerc, V. Murphy, M. Okazaki and G. C. Bazan, J. Am. Chem. Soc., 2002, 124, 15280; for recent review; (f) J. M. Lee, Y. Na, H. Han and S. Chang, Chem. Soc. Rev., 2004, 33, 302.
8. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
9. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
10. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
11. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
12. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
13. For recent examples, see (a) B. M. Nilsson and U. Hacksell, J. Heterocycl. Chem., 1989, 26, 269; (b) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; (c) A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett., 2001, 3, 2501; (d) A. G. M. Barrett, S. M. Cramp, A. J. Hennessy, P. A. Procopiou and R. S. Roberts, Org. Lett., 2001, 3, 271; (e) A. G. Godfrey, D. A. Brooks, L. A. Hay, M. Peters, J. R. McCarthy and D. Mitchell, J. Org. Chem., 2003, 68, 2623; (f) M. C. Bagley, J. W. Dale, X. Xiong and J. Bower, Org. Lett., 2003, 23, 4421.
14. The thiolate-bridged diruthenium complex (2a) was found to be an efficient catalyst for propargylic substitution reactions of propargylic alcohols with a variety of heteroatom-centred nucleophiles to give the corresponding functionalized propargylic products in high yields with a complete regioselectivity, (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26.
15. The thiolate-bridged diruthenium complex (2a) was found to be an efficient catalyst for propargylic substitution reactions of propargylic alcohols with a variety of heteroatom-centred nucleophiles to give the corresponding functionalized propargylic products in high yields with a complete regioselectivity, (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26.
16. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
17. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
18. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
19. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
20. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
21. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
22. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
23. For recent examples, see (a) P. A. Evans and J. E. Robinson, J. Am. Chem. Soc., 2001, 123, 4609; (b) B. M. Choudary, N. S. Chowdari, S. Madhi and M. L. Kantam, Angew. Chem., Int. Ed., 2001, 40, 4620; (c) J. L. Christopher, W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (d) T. Shimada, K. Mukaide, A. Shinohara, J. W. Han and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 1584; (e) J. Tian, N. Yamagiwa, S. Matsunaga and M. Shibasaki, Angew. Chem., Int. Ed., 2002, 41, 3636; (f) S. U. Son, K. H. Park and Y. K. Chung, J. Am. Chem. Soc., 2002, 124, 6838; (g) B. M. Trost and M. R. Machacek, Angew. Chem., Int. Ed., 2002, 41, 4693; (h) A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
24. 15NO [M] 201.1154. Found 201.1152.
25. 2): δ = 2.10 (s, 3 H), 4.14 (d, 1 H, J = 2.4 Hz), 4.70 (t, 1 H, J = 2.4 Hz), 5.49 (br, 1 H).
26. Detailed results of propargylic amidation along with the reaction mechanism will be published elsewhere. See reference 4.