Superior effect of a π-acceptor ligand (phosphine-electron-deficient olefin ligand) in the Negishi coupling involving alkylzinc reagents

Organic Letters

Volumn 9, Issue 22, 2007, Pages 4571-4574

  Luo, Xiancai ^a   Zhang, Heng ^a   Duan, Hui ^a   Liu, Qiang ^a   Zhu, Lizheng ^a   Zhang, Tony ^b   Lei, Aiwen ^a  

^a WUHAN UNIVERSITY   (China)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 35948988432     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701995t     Document Type: Article

References (33)

1. Negishi, E.-i.; Meijere, A. d. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002.
2. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710.
3. Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674-688.
4. Singh, R.; Nolan, S. P. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2006, 102, 168-196.
5. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
6. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
7. Cardenas, D. J. Angew. Chem., Int. Ed. 2003, 42, 384-387.
8. Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690-3693.
9. Navarro, O.; Kelly, R. A., III; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194-16195.
10. Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
11. Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028-13032.
12. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
13. Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10-11.
14. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411-2413.
15. Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719-2724.
16. Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 3805-3807.
17. Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. J. Org. Chem. 2005, 70, 8503-8507.
18. Campos K. R.; Klapars, A.; Waldman, J., H.; Dormer, P. G.; Chen, C.-y. J. Am. Chem. Soc. 2006, 128, 3538-3539.
19. Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398-3416.
20. Luh, T.-Y.; Leung, M.-k.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
21. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
22. Yamamoto, T.; Abla, M.; Murakami, Y. Bull. Chem. Soc. Jpn. 2002, 75, 1997-2009.
23. Jensen, A. E.; Knochel, P. J. Org. Chem. 2002, 67, 79-85.
24. Grundl, M. A.; Kennedy-Smith, J. J.; Trauner, D. Organometallics 2005, 24, 2831-2833.
25. Scrivanti, A.; Beghetto, V.; Matteoli, U.; Antonaroli, S.; Marini, A.; Crociani, B. Tetrahedron 2005, 61, 9752-9758.
26. Shintani, R.; Duan, W.-L.; Okamoto, K.; Hayashi, T. Tetrahedron: Asymmetry 2005, 16, 3400-3405.
27. Cardenas, D. J. Angew. Chem., Int. Ed. 1999, 38, 3018-3020.
28. Luh, T.-Y.; Leung, M.-k.; Wong, K.-T. Chem. Rev. 2000, 100, 3187-3204.
29. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F.; McGlacken, G. P.; Weissburger, F.; de Vries, A. H. M.; Schmieder-van de Vondervoort, L. Chem.-Eur. J. 2006, 12, 8750-8761.
30. Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048-15049.
31. Casares, J. A.; Espinet, P.; Fuentes, B.; Salas, G. J. Am. Chem. Soc. 2007, 129, 3508-3509.
32. 3 bond, in which the possible problem might be the reductive elimination and β-H elimination. ArI 3a, an electronic-deficient ArI, could be a good substrate for the oxidative addition. If the oxidative addition is fast enough and it is not the rate-determining step, we will have a chance to see the differences between ligand 1 and the others. (33) The reactions of cyclohexylzinc chloride and 2-iodoanisole or 4-iodoanisole produced the desired cross-coupling products in 34% and 48% isolated yields, respectively.
33. ArCl (electronic-deficient or electronic-rich) were not effective substrates at room temperature or 60 °C.