Palladium-catalyzed cross-coupling of unactivated alkenes with acrylates: Application to the synthesis of the C13-C21 fragment of palmerolide A

Chemistry - A European Journal

Volumn 18, Issue 42, 2012, Pages 13284-13287

  Wen, Zhen Kang ^a   Xu, Yun He ^a,b   Loh, Teck Peng ^a,b  

^a Nanyang Technological University   (Singapore)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

butadienes; C H bond functionalization; cross coupling; palladium; palmerolide A

Indexed keywords

CROSS-COUPLINGS; FUNCTIONALIZATIONS; HOMOALLYLIC ALCOHOL; PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS; PALLADIUM-CATALYZED CROSS-COUPLINGS; PALMEROLIDE A;

BUTADIENE; CATALYSIS; PALLADIUM; SALTS;

OLEFINS;

1,3 BUTADIENE DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALKENE; CARBON; HYDROGEN; MACROLIDE; PALLADIUM; PALMEROLIDE A;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ACRYLATES; ALKENES; BUTADIENES; CARBON; CATALYSIS; HYDROGEN; MACROLIDES; PALLADIUM;

EID: 84867195781     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201806     Document Type: Article

References (74)

1. F. Fringuelli, A. Taticchi, Dienes in the Diels-Alder Reaction, Wiley-Interscience, New York, 1990
2. T. Y. Luh, K.-T. Wong, Synthesis 1993, 349
3. G. Mehta, H. S. P. Rao, The Chemistry of Dienes and Polyenes, Vol. 1 (Ed:, Z. Rappoport,), Wiley, New York, 1997, pp. 359-480.
4. L. Horner, H. Hoffmann, H. G. Wippel, Chem. Ber. 1958, 91, 61
5. L. Horner, H. Hoffman, H. G. Wippel, G. Klahre, Chem. Ber. 1959, 92, 2499
6. W. S. Wadsworth, W. D. Emmons, J. Am. Chem. Soc. 1961, 83, 1733.
7. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
8. K. S. Yoo, C. H. Yoon, K. W. Jung, J. Am. Chem. Soc. 2006, 128, 16384
9. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
10. J. H. Delcamp, A. P. Brucks, M. C. White, J. Am. Chem. Soc. 2008, 130, 11270.
11. S. Yotphan, R. G. Bergman, J. E. Ellman, J. Am. Chem. Soc. 2008, 130, 2452
12. D. A. Colby, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2008, 130, 3645
13. Y. Shibata, Y. Otake, M. Hirano, K. Tanaka, Org. Lett. 2009, 11, 689.
14. T. Mitsudo, S. W. Zhang, M. Nagao, Y. Watanabe, J. Chem. Soc. Chem. Commun. 1991, 598
15. C. S. Yi, D. W. Lee, Y. Chen, Organometallics 1999, 18, 2043
16. F. Kakiuchi, T. Uetsuhara, Y. Tanaka, N. Chatani, S. Murai, J. Mol. Catal. A 2002, 182-183, 511
17. T. Nishimura, Y. Washitake, S. Uemura, Adv. Synth. Catal. 2007, 349, 2563.
18. K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374
19. R. F. Heck, J. P. Nolley, J. Org. Chem. 1972, 37, 2320
20. K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467
21. A. O. King, N. Okukado, E.-I. Negishi, J. Chem. Soc. Chem. Commun. 1977, 683
22. D. Milstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636
23. N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun. 1979, 866
24. Y. Hatanaka, T. Hiyama, J. Org. Chem. 1988, 53, 918.
25. Y. Fujiwara, I. Moritani, M. Matsuda, Tetrahedron 1968, 24, 4819
26. C. G. Jia, W. J. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097
27. C. G. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
28. D. J. Covell, N. A. Vermeulen, N. A. Labenz, M. C. White, Angew. Chem. 2006, 118, 8397
29. Angew. Chem. Int. Ed. 2006, 45, 8217
30. E. M. Stang, M. C. White, Nat. Chem. 2009, 1, 547
31. Y. Q. Feng, G. Chen, Angew. Chem. 2010, 122, 970
32. Angew. Chem. Int. Ed. 2010, 49, 958
33. D. H. Wang, J. Q. Yu, J. Am. Chem. Soc. 2011, 133, 5767
34. L. McMurray, F. O'Hara, M. J. Gaunt, Chem. Soc. Rev. 2011, 40, 1885
35. W. R. Gutekunst, P. S. Baran, Chem. Soc. Rev. 2011, 40, 1976.
36. N. P. Grimster, C. Cauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. 2005, 117, 3185
37. Angew. Chem. Int. Ed. 2005, 44, 3125
38. M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496
39. H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879
40. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
41. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
42. R. Giri, J. Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082
43. B. J. Li, S. D. Yang, Z. J. Shi, Synlett 2008, 949
44. L. Ackermann, Modern Arylation Methods, Wiley-VCH, Weinheim, 2009
45. X. Chen, K. M. Engle, D. H. Wang, J. Q. Yu, Angew. Chem. 2009, 121, 5196
46. Angew. Chem. Int. Ed. 2009, 48, 5094
47. S. Yanagisawa, K. Ueda, H. Sekizawa, K. Itami, J. Am. Chem. Soc. 2009, 131, 14622
48. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
49. B. Xiao, Y. Fu, J. Xu, T. J. Gong, J. J. Dai, J. Yi, L. Liu, J. Am. Chem. Soc. 2010, 132, 468
50. X. F. Wu, P. Anbarasan, H. Neumann, M. Beller, Angew. Chem. 2010, 122, 7474
51. Angew. Chem. Int. Ed. 2010, 49, 7316
52. C. Liu, H. Zhang, W. Shi, A. W. Lei, Chem. Rev. 2011, 111, 1780
53. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
54. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
55. L. Ackermann, S. Fenner, Chem. Commun. 2011, 47, 430
56. X. S. Wang, D. Leow, J. Q. Yu, J. Am. Chem. Soc. 2011, 133, 13864.
57. G. Oehme, H. Pracejus, Tetrahedron Lett. 1979, 20, 343
58. W. A. Nugent, F. W. J. Hobbs, J. Org. Chem. 1983, 48, 5364
59. D. Neibecker, P. Grenouillet, I. Tkatchenko, Organometallics 1984, 3, 1130
60. I. Guibert, D. Neibecker, I. Tkatchenko, J. Chem. Soc. Chem. Commun. 1989, 1850.
61. Y. Hatamoto, S. Sakaguchi, Y. Ishii, Org. Lett. 2004, 6, 4623.
62. H. Yu, W. Jin, C. Sun, J. Chen, W. Du, S. He, Z. Yu, Angew. Chem. 2010, 122, 5928
63. Angew. Chem. Int. Ed. 2010, 49, 5792.
64. T. Besset, N. Kuhl, F. W. Patureau, F. Glorius, Chem. Eur. J. 2011, 17, 7167.
65. Y. H. Xu, J. Lu, T. P. Loh, J. Am. Chem. Soc. 2009, 131, 1372.
66. T. Diyabalanage, C. D. Amsler, J. B. McClintock, B. J. Baker, J. Am. Chem. Soc. 2006, 128, 5630.
67. K. C. Nicolaou, R. Guduru, Y. P. Sun, B. Banerji, D. Y.-K. Chen, Angew. Chem. 2007, 119, 6000
68. Angew. Chem. Int. Ed. 2007, 46, 5896
69. K. C. Nicolaou, Y. P. Sun, R. Guduru, B. Banerji, D. Y.-K. Chen, J. Am. Chem. Soc. 2008, 130, 3633
70. X. Jiang, B. Liu, S. Lebreton, J. K. De Brabander, J. Am. Chem. Soc. 2007, 129, 6386
71. M. Penner, V. Rauniyar, L. T. Kaspar, D. G. Hall, J. Am. Chem. Soc. 2009, 131, 14216.
72. J. L. Luo, H. M. Li, J. L. Wu, X. L. Xing, W. M. Dai, Tetrahedron 2009, 65, 6828
73. A. B. Smith III, Y. Qiu, D. R. Jones, K. Kobayashi, J. Am. Chem. Soc. 1995, 117, 12011
74. K. A. Scheidt, T. D. Bannister, A. Tasaka, M. D. Wendt, B. M. Savall, G. J. Fegley, W. R. Roush, J. Am. Chem. Soc. 2002, 124, 6981.