Highly selective palladium-catalyzed oxidative Csp2-Csp 3 cross-coupling of arylzinc and alkylindium reagents through double transmetallation

Advanced Synthesis and Catalysis

Volumn 351, Issue 4, 2009, Pages 630-634

  Jin, Liqun ^a   Zhao, Yingsheng ^a   Zhu, Lizheng ^a   Zhang, Heng ^a   Lei, Aiwen ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Alkylindium reagents; Arylzinc reagents; Cross coupling reaction; Palladium

Indexed keywords

EID: 62549088775     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800703     Document Type: Article

References (46)

1. ndedn., Volume 2, Wiley-VCH, Weinhaim, 2004.
2. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 1984, 106, 158-163.
3. J. Liu, Y. Deng, H. Wang, H. Zhang, G. Yu, B. Wu, H. Zhang, Q. Li, T. B. Marder, Z. Yang, A. Lei, Org. Lett. 2008, 10, 2661-2664.
4. H. Wang, J. Liu, Y. Deng, T. Min, G. Yu, X. Wu, Z. Yang, A. Lei, Chem. Eur. J. 2009, 15, 1499-1507.
5. S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676-4701;
6. Angew. Chem. Int. Ed. 2001, 40, 4544-4568.
7. D. J. Cárdenas, Angew. Chem. 1999, 111, 3201-3203;
8. Angew. Chem. Int. Ed. 1999, 38, 3018-3020.
9. D. J. Cárdenas, Angew. Chem. 2003, 115, 398-401;
10. Angew. Chem. Int. Ed. 2003, 42, 384-387.
11. A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680-695;
12. Angew. Chem. Int. Ed. 2005, 44, 674-688.
13. T.-Y. Luh, M.-K. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187-3204.
14. N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566.
15. D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
16. G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821;
17. Angew. Chem. Int. Ed. 2003, 42, 3690-3693.
18. O. Navarro, R. A. Kelly, III, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194-16195.
19. M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 13642-13643.
20. J. E. Milne, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 13028-13032.
21. B. C. Hamann, J. F. Hartwig, J. Am. Chem. Soc. 1998, 120, 7369-7370.
22. A. F. Littke, G. C. Fu, Angew. Chem. 1999, 111, 2568-2570;
23. Angew. Chem. Int. Ed. 1999, 38, 2411-2413.
24. C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719-2724.
25. N. Hadei, E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Org. Lett. 2005, 7, 3805-3807.
26. K. R. Campos, A. Klapars, J. H. Waldman, P. G. Dormer, C. -y Chen, J. Am. Chem. Soc. 2006, 128, 3538-3539.
27. Z. Xue, D. Yang, C. Wang, J. Organomet. Chem. 2006, 691, 247-250.
28. V. Farina, B. Krishnan, D. R. Marshall, G. P. Roth, J. Org. Chem. 1993, 55, 5434-5444.
29. K. Lee, J. Lee, P. H. Lee, J. Org. Chem. 2002, 67, 8265-8268.
30. M. A. Pena, J. P. Sestelo, L. A. Sarandeses, J. Org. Chem. 2007, 72, 1271-1275.
31. P. H. Lee, S. Sung, K. Lee, Org. Lett. 2001, 3, 3201-3204.
32. R. Riveiros, D. Rodriguez, J. Perez Sestelo, L. A. Sar-andeses, Org. Lett. 2006, 8, 1403-1406.
33. C. Croix, A. Balland-Longeau, A. Duchene, J. Thibonnet, Synth. Commun. 2006, 36, 3261-3270.
34. M. A. Pena, J. P. Sestelo, L. A. Sarandeses, Synthesis 2005, 485-492.
35. K. Takami, S. Mikami, H. Yorimitsu, H. Shinokubo, K. Oshima, J. Org. Chem. 2003, 68, 6627-6631.
36. P. H. Lee, S. W. Lee, K. Lee, Org. Lett. 2003, 5, 1103-1106.
37. I. Perez, J. P. Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155-4160.
38. I. Perez, J. Perez Sestelo, L. A. Sarandeses, Org. Lett. 1999, 1, 1267-1269.
39. I. Perez, J. Perez Sestelo, M. A. Maestro, A. Mourino, L. A. Sarandeses, J. Org. Chem. 1998, 63, 10074-10076.
40. An alternative mechanism in which the Zn transmetallation precedes the In one may also be possible but could not be differentiated in this case.
41. C. Adamo, C. Amatore, I. Ciofini, A. Jutand, H. Lakmini, J. Am. Chem. Soc. 2006, 128, 6829-6836.
42. A. Lei, X. Zhang, Tetrahedron Lett. 2002, 43, 2525-2528.
43. O. T. Beachley, Jr., D.J. MacRae, M. R. Churchill, A. Y. Kovalevsky, E. S. Robirds, Organometallics 2003, 22, 3991-4000.
44. J. Chen, G. Lei, W. Xu, X. Jin, M. Shao, Y. Tang, J. Or-ganomet. Chem. 1985, 256, 55-67.
45. L. S. Chen, G. J. Chen, C. Tamborski, J. Organomet. Chem. 1983, 251, 139-148.
46. L. S. Chen, G. J. Chen, C. Tamborski, J. Organomet. Chem. 1981, 215, 281-291.