Palladium-catalyzed cross-coupling of internal alkenes with terminal alkenes to functionalized 1,3-butadienes using C-H bond activation: Efficient synthesis of bicyclic pyridones

Angewandte Chemie - International Edition

Volumn 49, Issue 33, 2010, Pages 5792-5797

  Yu, Haifeng ^a,b   Jin, Weiwei ^a   Sun, Chenglin ^a   Chen, Jiping ^a   Du, Wangmin ^a   He, Songbo ^a   Yu, Zhengkun ^a,c  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b ANSHAN NORMAL UNIVERSITY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkenes; Alkenylation; C H activation; Heterocycles; Palladium

Indexed keywords

ALKENYLATION; C-H ACTIVATION; CH-BOND ACTIVATION; CHEMICAL EQUATIONS; CROSS-COUPLINGS; DITHIOACETALS; EFFICIENT SYNTHESIS; FUNCTIONALIZED; HETEROCYCLES PALLADIUM; PALLADIUM-CATALYZED CROSS-COUPLINGS; PYRIDONES; REGIO-SELECTIVE; TERMINAL ALKENES;

ACTIVATION ANALYSIS; BUTADIENE; CHEMICAL BONDS; CHEMICAL REACTIONS; PALLADIUM;

OLEFINS;

EID: 77955318706     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002737     Document Type: Article

References (45)

1. For selected recent reviews, see: a) L. M. Xu, B. J. Li, Z. Yang, Z. J. Shi, Chem. Soc. Rev. 2010, 39, 712;
2. b) L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976;
3. Angew. Chem. Int. Ed. 2009, 48, 9792;
4. c) X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196;
5. Angew. Chem. Int. Ed. 2009, 48, 5094.
6. D. J. Dong, H. H. Li, S. K. Tian, J. Am. Chem. Soc. 2010, 132, 5018.
7. C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027.
8. G. A. Molander, B. Canturk, Angew. Chem. 2009, 121, 9404;
9. Angew. Chem. Int. Ed. 2009, 48, 9240.
10. G. Fridkin, N. Boutard, W. D. Lubell, J. Org. Chem. 2009, 74, 5603.
11. R. Tanaka, K. Noguchi, K. Tanaka, J. Am. Chem. Soc. 2010, 132, 1238.
12. J. Sakurada, T. Satoh, Tetrahedron 2007, 63, 3806.
13. E.-I. Negishi, Z. H. Huang, G. W. Wang, S. Mohan, C. Wang, H. Hattori, Acc. Chem. Res. 2008, 41, 1474.
14. R. E. Shade,A. M. Hyde, J.-C. Olsen, C. A. Merlic, J. Am. Chem. Soc. 2010, 132, 1202.
15. J. J. Mousseau, J. A. Bull, A. B. Charette, Angew. Chem. 2010, 122, 1133;
16. Angew. Chem. Int. Ed. 2010, 49, 1115.
17. Y. Matsuura, M. Tamura, T. Kochi, M. Sato, N. Chatani, F. Kakiuchi, J. Am. Chem. Soc. 2007, 129, 9858.
18. A. Arcadi, M. Alfonsi, F. Marinelli, J. Organomet. Chem. 2007, 692, 5322.
19. Selected recent reports, see: a) D.-H. Wang, K. M. Engle, B.-F. Shi, J.-Q. Yu, Science 2010, 327, 315;
20. b) M.Wasa, K. M. Engle, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3680;
21. c) B.-F. Shi, Y.-H. Zhang, J. K. Lam,D.-H.Wang, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 460;
22. d) J. L.Wu, X. L. Cui, L. M. Chen, G. J. Jiang, Y. J.Wu, J. Am. Chem. Soc. 2009, 131, 13888;
23. e) A. García-Rubia, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2009, 121, 6633;
24. Angew. Chem. Int. Ed. 2009, 48, 6511.
25. H. Zhou, Y.-H. Xu, W.-J. Chung, T.-P. Loh, Angew. Chem. 2009, 121, 5459;
26. Angew. Chem. Int. Ed. 2009, 48, 5355.
27. Y.-H. Zhang, B.-F. Shi, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 5072.
28. a) Y. Hatamoto, S. Sakaguchi, Y. Ishii, Org. Lett. 2004, 6, 4623;
29. b) Y.-H. Xu, J. Lu, T.-P. Loh, J. Am. Chem. Soc. 2009, 131, 1372.
30. C. Schotes, A. Mezzetti, J. Am. Chem. Soc. 2010, 132, 3652.
31. C. Vovard-Le Bray, S. Drien, P. Dixneuf, Angew. Chem. 2009, 121, 1467;
32. Angew. Chem. Int. Ed. 2009, 48, 1439.
33. T. Kobatake, S. Yoshida, H. Yorimitsu, K. Oshima, Angew. Chem. 2010, 122, 2390;
34. Angew. Chem. Int. Ed. 2010, 49, 2340.
35. For selected recent reports, see: a) H. F. Yu, Z. K. Yu, Angew. Chem. 2009, 121, 2973;
36. Angew. Chem. Int. Ed. 2009, 48, 2929;
37. b) J. Tan, X. X. Xu, L. J. Zhang, Y. F. Li, Q. Liu, Angew. Chem. 2009, 121, 2912;
38. Angew. Chem. Int. Ed. 2009, 48, 2868;
39. c) P. P. Singh, A. K. Yadav, H. Ila, H, Junjappa, J. Org. Chem. 2009, 74, 5496.
40. a) L. A. Smyth, T. P. Matthews, P. N. Horton, M. B. Hursthouse, I. Collins, Tetrahedron 2010, 66, 2843;
41. b) L. A. Marcaurelle, C. Johannes, D. Yohannes, B. P. Tillotson, D. Mann, Bioorg. Med. Chem. Lett. 2009, 19, 2500.
42. M. X. Zhao, M. X. Wang, Z. T. Huang, Tetrahedron 2002, 58, 1309.
43. D. G. Hehemann,W.Winnik, J. Heterocycl. Chem. 1994, 31, 393.
44. D. C. Cheng, L. Croft, M. Abdi, A. Lightfoot, T. Gallagher, Org. Lett. 2007, 9, 5175.
45. D. C. Cheng, T. Gallagher, Org. Lett. 2009, 11, 2639.