Palladium-catalyzed cross-couplings of unsaturated halides bearing relatively acidic hydrogen atoms with organozinc reagents

Synthesis

Volumn , Issue 4, 2009, Pages 681-686

  Dong, Zhibing ^a,b   Manolikakes, Georg ^a   Li, Jinshan ^b   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b NANKAI UNIVERSITY   (China)

Author keywords

Cross coupling; Functionalized zinc reagents; Palladium catalysis; Polyfunctional biaryls

Indexed keywords

ARYL HALIDES; BENZYLIC; CROSS-COUPLING; FUNCTIONALIZED ZINC REAGENTS; HYDROGEN ATOMS; ORGANOZINC REAGENTS; PALLADIUM ACETATES; PALLADIUM CATALYSIS; PALLADIUM-CATALYZED CROSS-COUPLINGS; POLYFUNCTIONAL BIARYLS; PROTECTING GROUPS; ZINC REAGENTS;

BEARINGS (STRUCTURAL); CATALYSIS; HYDROGEN; PALLADIUM; PALLADIUM COMPOUNDS; ZINC;

ORGANOMETALLICS;

HALIDE; HYDROGEN; HYDROXIDE; PALLADIUM; PALLADIUM ACETATE; PROTON; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION;

EID: 63849336084     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083286     Document Type: Article

References (27)

1. (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
2. (b) Tsuji, J. Transition Metal Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: Chichester, 1995.
3. (c) Transition Metals for Organic Synthesis, 2nd ed.; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
4. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. (b) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387.
6. (c) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413.
7. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem. Int. Ed. 2000, 39, 4153.
8. (e) Molander, G. A.; Biolatto, B. J. Org. Chem. 2003, 68, 4302.
9. (a) Handy, S. T.; Zhang, Y.; Bregman, H. J. Org. Chem. 2004, 69, 2362.
10. (b) Chaumeil, H.; Signorella, S.; Le Drian, C. Tetrahedron 2000, 56, 9655.
11. (c) Wanatabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
12. (a) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
13. (b) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
14. (c) Zeng, X.; Quian, M.; Hu, Q.; Negishi, E. Angew. Chem. Int. Ed. 2004, 43, 2259.
15. For selected examples from our group, see: (a) Sase, S.; Jaric, M.; Metzger, A.; Malakhov, V.; Knochel, P. J. Org. Chem. 2008, 73, 7380.
16. (b) Gavryushin, A.; Kofink, C.; Manolikakes, G.; Knochel, P. Org. Lett. 2005, 7, 4871.
17. Manolikakes, G.; Schade, M. A.; Munoz Hernandez, C.; Mayr, H.; Knochel, P. Org. Lett. 2008, 10, 2765.
18. (a) Altman, R. A.; Buchwald, S. L. Nature Protocols 2007, 2, 3115.
19. (b) Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 5096.
20. (c) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
21. (d) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
22. Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2006, 45, 6040.
23. a data see http://www.chem.wisc.edu/areas/reich/pkatable/index.htm and references cited therein.
24. For the possible use of thioarylaminyls as spin source or building block for organic magnets, see: Magnetic Properties of Organic Materials; Lathi, P. M., Ed.; Marcel Dekker: New York, 1999.
25. Metzger, A.; Schade, M. A.; Knochel, P. Org. Lett. 2008, 10, 1107.
26. Our experiments indicate a relative kinetic basicity of zinc reagents: arylzinc halide > alkylzinc halide > benzylic zinc halide. For further experimental details, see ref. 7.
27. Krasovskiy, A.; Knochel, P. Synthesis 2006, 890.