Room temperature nickel(0)-catalyzed Suzuki-Miyaura cross-couplings of activated alkenyl tosylates: Efficient synthesis of 4-substituted coumarins and 4-substituted 2(5H)-furanones

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1635-1637

  Tang, Zhen Yu ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Arylboronic acids; Cross coupling; Nickel; Phosphane ligand; Tosylates

Indexed keywords

ALKENYL GROUP; COUMARIN DERIVATIVE; FURANONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; MOLECULAR DYNAMICS; ROOM TEMPERATURE; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 12344317890     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404150     Document Type: Article

References (28)

1. Selected recent reports on coumarins: a) L. Xie, Y. Takeuchi, L. M. Cosentino, A. T. McPhail, K.-H. Lee, J. Med. Chem. 2001, 44, 664-671; b) A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, H. Ohigashi, Bioorg. Med. Chem. Lett. 2000, 10, 59-62; c) Y. Fall, C. Teran, M. Teijeira, L. Santana, E. Uriarte, Synthesis 2000, 643-645; d) A. J. Vlietinck, T. De Bruyne, S. Apers, L. A. Pieters. Planta Med. 1998, 64, 97-109.
2. Selected recent reports on coumarins: a) L. Xie, Y. Takeuchi, L. M. Cosentino, A. T. McPhail, K.-H. Lee, J. Med. Chem. 2001, 44, 664-671; b) A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, H. Ohigashi, Bioorg. Med. Chem. Lett. 2000, 10, 59-62; c) Y. Fall, C. Teran, M. Teijeira, L. Santana, E. Uriarte, Synthesis 2000, 643-645; d) A. J. Vlietinck, T. De Bruyne, S. Apers, L. A. Pieters. Planta Med. 1998, 64, 97-109.
3. Selected recent reports on coumarins: a) L. Xie, Y. Takeuchi, L. M. Cosentino, A. T. McPhail, K.-H. Lee, J. Med. Chem. 2001, 44, 664-671; b) A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, H. Ohigashi, Bioorg. Med. Chem. Lett. 2000, 10, 59-62; c) Y. Fall, C. Teran, M. Teijeira, L. Santana, E. Uriarte, Synthesis 2000, 643-645; d) A. J. Vlietinck, T. De Bruyne, S. Apers, L. A. Pieters. Planta Med. 1998, 64, 97-109.
4. Selected recent reports on coumarins: a) L. Xie, Y. Takeuchi, L. M. Cosentino, A. T. McPhail, K.-H. Lee, J. Med. Chem. 2001, 44, 664-671; b) A. Murakami, G. Gao, M. Omura, M. Yano, C. Ito, H. Furukawa, D. Takahashi, K. Koshimizu, H. Ohigashi, Bioorg. Med. Chem. Lett. 2000, 10, 59-62; c) Y. Fall, C. Teran, M. Teijeira, L. Santana, E. Uriarte, Synthesis 2000, 643-645; d) A. J. Vlietinck, T. De Bruyne, S. Apers, L. A. Pieters. Planta Med. 1998, 64, 97-109.
5. Selected recent reports on 2(5H)-furanones and derivatives: a) F. Bellina, C. Anselmi, S. Viel, L. Mannia, R. Rossi, Tetrahedron, 2001, 57, 9997-10007 and references cited therein; b) M. J. Ortega, E. Zubía, J. M. Ocaña, S. Naranjo, J. Salvá Tetrahedron, 2000, 56, 3963-3967; c) T. Honda, H. Mizutani, K. Kanai, J. Org. Chem. 1996, 61, 9374-9378; d) S. L. Midland, N. T. Keen, J. J. Sims, J. Org. Chem. 1995, 60, 1118-1119.
6. Selected recent reports on 2(5H)-furanones and derivatives: a) F. Bellina, C. Anselmi, S. Viel, L. Mannia, R. Rossi, Tetrahedron, 2001, 57, 9997-10007 and references cited therein; b) M. J. Ortega, E. Zubía, J. M. Ocaña, S. Naranjo, J. Salvá Tetrahedron, 2000, 56, 3963-3967; c) T. Honda, H. Mizutani, K. Kanai, J. Org. Chem. 1996, 61, 9374-9378; d) S. L. Midland, N. T. Keen, J. J. Sims, J. Org. Chem. 1995, 60, 1118-1119.
7. Selected recent reports on 2(5H)-furanones and derivatives: a) F. Bellina, C. Anselmi, S. Viel, L. Mannia, R. Rossi, Tetrahedron, 2001, 57, 9997-10007 and references cited therein; b) M. J. Ortega, E. Zubía, J. M. Ocaña, S. Naranjo, J. Salvá Tetrahedron, 2000, 56, 3963-3967; c) T. Honda, H. Mizutani, K. Kanai, J. Org. Chem. 1996, 61, 9374-9378; d) S. L. Midland, N. T. Keen, J. J. Sims, J. Org. Chem. 1995, 60, 1118-1119.
8. Selected recent reports on 2(5H)-furanones and derivatives: a) F. Bellina, C. Anselmi, S. Viel, L. Mannia, R. Rossi, Tetrahedron, 2001, 57, 9997-10007 and references cited therein; b) M. J. Ortega, E. Zubía, J. M. Ocaña, S. Naranjo, J. Salvá Tetrahedron, 2000, 56, 3963-3967; c) T. Honda, H. Mizutani, K. Kanai, J. Org. Chem. 1996, 61, 9374-9378; d) S. L. Midland, N. T. Keen, J. J. Sims, J. Org. Chem. 1995, 60, 1118-1119.
9. For recent examples: a) D. V. Kadnikov, R. C. Larock, Org. Lett. 2000, 2, 3643-3646; b) M.-L. Yao, M.-Z. Deng, Heteroatom Chem. 2000, 11, 380-382.
10. For recent examples: a) D. V. Kadnikov, R. C. Larock, Org. Lett. 2000, 2, 3643-3646; b) M.-L. Yao, M.-Z. Deng, Heteroatom Chem. 2000, 11, 380-382.
11. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-(p-toluenesulfonyl)- or 4-halocoumarins: a) J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397; b) J. Wu, Z.Yang, J. Org. Chem. 2001, 66, 7875-7878; c) J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642-3645; d) L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545; e) G. M. Boland, D. M. X. Donnelly, J.-P Finet, M. D. Rea, J. Chem. Soc. Perkin Trans. 1 1996, 2591-2597.
12. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-(p-toluenesulfonyl)- or 4-halocoumarins: a) J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397; b) J. Wu, Z.Yang, J. Org. Chem. 2001, 66, 7875-7878; c) J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642-3645; d) L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545; e) G. M. Boland, D. M. X. Donnelly, J.-P Finet, M. D. Rea, J. Chem. Soc. Perkin Trans. 1 1996, 2591-2597.
13. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-(p-toluenesulfonyl)- or 4-halocoumarins: a) J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397; b) J. Wu, Z.Yang, J. Org. Chem. 2001, 66, 7875-7878; c) J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642-3645; d) L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545; e) G. M. Boland, D. M. X. Donnelly, J.-P Finet, M. D. Rea, J. Chem. Soc. Perkin Trans. 1 1996, 2591-2597.
14. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-(p-toluenesulfonyl)- or 4-halocoumarins: a) J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397; b) J. Wu, Z.Yang, J. Org. Chem. 2001, 66, 7875-7878; c) J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642-3645; d) L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545; e) G. M. Boland, D. M. X. Donnelly, J.-P Finet, M. D. Rea, J. Chem. Soc. Perkin Trans. 1 1996, 2591-2597.
15. For recent examples of Pd(0)- or Ni(0)-catalyzed cross-couplings of 4-(p-toluenesulfonyl)- or 4-halocoumarins: a) J. Wu, L. Wang, R. Fathi, Z. Yang, Tetrahedron Lett. 2002, 43, 4395-4397; b) J. Wu, Z.Yang, J. Org. Chem. 2001, 66, 7875-7878; c) J. Wu, Y. Liao, Z. Yang, J. Org. Chem. 2001, 66, 3642-3645; d) L. Schio, F. Chatreaux, M. Klich, Tetrahedron Lett. 2000, 41, 1543-1545; e) G. M. Boland, D. M. X. Donnelly, J.-P Finet, M. D. Rea, J. Chem. Soc. Perkin Trans. 1 1996, 2591-2597.
16. For a report on Suzuki-Miyaura coupling reactions involving other vinyl tosylates: M. A. Huffman, N. Yasuda, Synlett 1999, 471-473.
17. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans. 1 1996, 1913-1919.
18. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans, 1 1996, 1913-1919.
19. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans, 1 1996, 1913-1919.
20. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans, 1 1996, 1913-1919.
21. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans, 1 1996, 1913-1919.
22. For recent examples: a) P. Forgione, D. Wilson, A. G. Fallis Tetrahedron Lett. 2000, 41, 17-20; b) R. Maon, A. M. E. Richecoeur, J. B. Sweeney, J. Org. Chem. 1999, 64, 328-329; c) S. Ma, Z. Shi J. Org. Chem. 1998, 63, 6387-6389; d) W.-J. Xiao, H. Alper J. Org. Chem. 1997, 62, 3422-3423; e) J. A. Marshall, M. A. Wolf J. Org. Chem. 1996, 61, 3238-3239; f) G. J. Hollingworth, G. Perkins, J. B. Sweeney, J. Chem. Soc. Perkin Trans, 1 1996, 1913-1919.
23. For recent examples of Pd(0)- or Ni(0)-catalyzed 4-substituted 2(5H)-furanone syntheses from 4-halo- or 4-sulfonyloxy-2(5H)-furanones: a) J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673; b) R. Rossi, F. Bellina, E. Raugei, E. Synlett 2000, 1749-1752; c) M.-L. Yao, M.-Z. Deng, J. Org. Chem. 2000, 65, 5034-5036; d) J. Boukouvalas, N. Lachance, M. Ouellet, M. Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668.
24. For recent examples of Pd(0)- or Ni(0)-catalyzed 4-substituted 2(5H)-furanone syntheses from 4-halo- or 4-sulfonyloxy-2(5H)-furanones: a) J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673; b) R. Rossi, F. Bellina, E. Raugei, E. Synlett 2000, 1749-1752; c) M.-L. Yao, M.-Z. Deng, J. Org. Chem. 2000, 65, 5034-5036; d) J. Boukouvalas, N. Lachance, M. Ouellet, M. Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668.
25. For recent examples of Pd(0)- or Ni(0)-catalyzed 4-substituted 2(5H)-furanone syntheses from 4-halo- or 4-sulfonyloxy-2(5H)-furanones: a) J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673; b) R. Rossi, F. Bellina, E. Raugei, E. Synlett 2000, 1749-1752; c) M.-L. Yao, M.-Z. Deng, J. Org. Chem. 2000, 65, 5034-5036; d) J. Boukouvalas, N. Lachance, M. Ouellet, M. Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668.
26. For recent examples of Pd(0)- or Ni(0)-catalyzed 4-substituted 2(5H)-furanone syntheses from 4-halo- or 4-sulfonyloxy-2(5H)-furanones: a) J. Wu, Q. Zhu, L. Wang, R. Fathi, Z. Yang, J. Org. Chem. 2003, 68, 670-673; b) R. Rossi, F. Bellina, E. Raugei, E. Synlett 2000, 1749-1752; c) M.-L. Yao, M.-Z. Deng, J. Org. Chem. 2000, 65, 5034-5036; d) J. Boukouvalas, N. Lachance, M. Ouellet, M. Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668.
27. Z.-Y. Tang, Q.-S. Hu, J. Am. Chem. Soc. 2004, 126, 3058-3059.
28. K. W. Barnett, J. Chem. Educ. 1974, 51, 422-423.