Palladium-Catalyzed R(sp3)-Zn/R(sp)-SnBu3 Oxidative Cross-Coupling

Liqun Jin; Yingsheng Zhao; Haibo Wang; Aiwen Lei

doi:10.1055/s-2007-990863

PSP

Palladium-Catalyzed R(sp³)-Zn/R(sp)-SnBu₃ Oxidative Cross-Coupling

Liqun Jin, Yingsheng Zhao, Haibo Wang, Aiwen Lei*
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, P. R. of China
Fax: +86(27)68754067; e-Mail: aiwenlei@whu.edu.cn;

Abstract

All articles of this category

Abstract

A novel bond formation through oxidative cross-coupling with desyl chloride as the oxidant has been investigated. The coupling can be carried out under mild conditions. The Csp³-center carbon was involved even in the presence of a β-H, and up to 90% of the desired cross-coupling product was obtained with the secondary Csp³-center substrate.

Key words

oxidative cross-coupling - transmetalation - organotin reagents - organozinc reagents - palladium

Full Text

References

1 Crabtree RH. The Organometallic Chemistry of the Transition Metals 3rd ed.: Wiley; New York: 2001.

2 Negishi E.-i. de Meijere A. Handbook of Organopalladium Chemistry for Organic Synthesis Wiley-Interscience; New York: 2002.

3 Tsuji J. Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis Wiley; Chichester: 2000.

4 de Meijere A. Diederich F. Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: Wiley-VCH; Weinheim: 2004.

5 Tamao K. Kiso Y. Sumitani K. Kumada M. J. Am. Chem. Soc. 1972, 94: 9268

6 Tamao K. Sumitani K. Kumada M. J. Am. Chem. Soc. 1972, 94: 4374

7 Negishi E. Okukado N. King AO. Van Horn DE. Spiegel BI. J. Am. Chem. Soc. 1978, 100: 2254

8 King AO. Okukado N. Negishi E. J. Chem. Soc., Chem. Commun. 1977, 683

9 Miyaura N. Suzuki A. J. Chem. Soc., Chem. Commun. 1979, 866

10 Stille JK. Pure Appl. Chem. 1985, 57: 1771

11 Kataoka N. Shelby Q. Stambuli JP. Hartwig JF. J. Org. Chem. 2002, 67: 5553

12 Old DW. Wolfe JP. Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722

13 Cardenas DJ. Angew. Chem. Int. Ed. 2003, 42: 384

14 Altenhoff G. Goddard R. Lehmann CW. Glorius F. Angew. Chem. Int. Ed. 2003, 42: 3690

15 Navarro O. Kelly RA. Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194

16 Eckhardt M. Fu GC. J. Am. Chem. Soc. 2003, 125: 13642

17 Milne JE. Buchwald SL. J. Am. Chem. Soc. 2004, 126: 13028

18 Hamann BC. Hartwig JF. J. Am. Chem. Soc. 1998, 120: 7369

19 Littke AF. Fu GC. J. Org. Chem. 1999, 64: 10

20 Littke AF. Fu GC. Angew. Chem. Int. Ed. 1999, 38: 2411

21 Dai C. Fu GC. J. Am. Chem. Soc. 2001, 123: 2719

22 Hadei N. Kantchev EAB. O’Brien CJ. Organ MG. Org. Lett. 2005, 7: 3805

23 Hadei N. Kantchev EAB. O’Brien CJ. Organ MG. J. Org. Chem. 2005, 70: 8503

24 Campos KR. Klapars A. Waldman JH. Dormer PG. Chen C.-y. J. Am. Chem. Soc. 2006, 128: 3538

25 Barrios-Landeros F. Hartwig JF. J. Am. Chem. Soc. 2005, 127: 6944

26 Hills ID. Netherton MR. Fu GC. Angew. Chem. Int. Ed. 2003, 42: 5749

27 Littke AF. Fu GC. Angew. Chem. Int. Ed. 1999, 37: 3387

28 Collman JP. Hegedus LS. Principles and Applications of Organotransition Metal Chemistry, 2nd ed. University Science Books; Mill Valley, CA: 1987.

29 Luh T.-Y. Leung M.-k. Wong K.-T. Chem. Rev. 2000, 100: 3187

30 Cardenas DJ. Angew. Chem. Int. Ed. 1999, 38: 3018

31 Culkin DA. Hartwig JF. Organometallics 2004, 23: 3398

32 Casares JA. Espinet P. Fuentes B. Salas G. J. Am. Chem. Soc. 2007, 129: 3508

33 Devasagayaraj A. Stuedemann T. Knochel P. Angew. Chem., Int. Ed. Engl. 1996, 34: 2723

34 Jensen AE. Knochel P. J. Org. Chem. 2002, 67: 79

35 Giovannini R. Stuedemann T. Devasagayaraj A. Dussin G. Knochel P. J. Org. Chem. 1999, 64: 3544

36 Giovannini R. Knochel P. J. Am. Chem. Soc. 1998, 120: 11186

37 Giovannini R. Studemann T. Dussin G. Knochel P. Angew. Chem. Int. Ed. 1998, 37: 2387

38 Zhao Y. Wang H. Hou X. Hu Y. Lei A. Zhang H. Zhu L. J. Am. Chem. Soc. 2006, 128: 15048

39 Lei A. Srivastava M. Zhang X. J. Org. Chem. 2002, 67: 1969

40 Lei A. Zhang X. Org. Lett. 2002, 4: 2285

41 Lei A. Zhang X. Tetrahedron Lett. 2002, 43: 2525

42 Moloney MG. Pinhey JT. Roche EG. J. Chem. Soc., Perkin Trans. 1 1989, 333

43 Djakovitch L. Wagner M. Hartung CG. Beller M. Koehler K. J. Mol. Catal. A: Chem. 2004, 219: 121

44 Knochel P. Jones P. Organozinc Reagents: A Practical Approach Oxford University Press; Oxford: 1999.

45

The desired cross-coupling product was mixed with 1,2-diphenylethanone, which was formed from the Zn-enolate IV. Efforts to completely separate the two compounds were unsuccessful.