A very simple synthesis of chloroalkenes and chlorodienes by selective Suzuki couplings of 1,1- and 1,2-dichloroethylene

Advanced Synthesis and Catalysis

Volumn 348, Issue 3, 2006, Pages 347-353

  Barluenga, José ^a   Moriel, Patricia ^a   Aznar, Fernando ^a   Valdés, Carlos ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

Boronic acids; Chloroalkenes; Cross coupling; Palladium; Suzuki reaction

Indexed keywords

EID: 33644597578     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505302     Document Type: Article

References (41)

1. For general reviews on Pd-catalyzed cross-coupling reactions, see: a) E. Negishi, (Ed.), Handbook of Organopalladium Chemistry for Organic Synthesis, Wiley-Interscience, New York, 2002, Vol. I, Part III, pp 215-1119;
2. b) A. de Meijere, F. Diederich, (Eds.), Metal-Catalyzed Cross Coupling Reactions, VCH, Weinheim, 2004.
3. a) J. Barluenga, F. Aznar, M. A. Fernández, C. Valdés, Chem. Commun. 2002, 2362-2363;
4. b) J. Barluenga, M. A. Fernández, F. Aznar, C. Valdés, Chem. Eur. J. 2004, 10, 494-507;
5. c) J. Barluenga, F. Aznar, M. A. Fernández, C. Valdés, Chem. Commun. 2004, 1400-1401.
6. J. Barluenga, F. Aznar, P. Moriel, C. Valdés, Adv. Synth. Catal. 2004, 346, 1697.
7. For a review on the synthesis and application of hetero-substituted dienes, see: J. Barluenga, A. Suárez-Sobrino, L. A. López, Aldrichim. Acta 1999, 32, 4.
8. a) E. Nagashima, K. Suzuki, M. i. Ishikawa, M. Sekiya, Heterocycles, 1985, 23, 1873-1879;
9. b) R. Baati, D. K. Barma, U. M. Krishna, C. Mioskowski, J. R. Falck, Tetrahedron Lett. 2002, 43, 959-961;
10. c) B. Crousse, M. Mladenova, P. Ducept, M. Alami, G. Linstrumelle, Tetrahedron 1999, 55, 4353-4368 and references cited therein.
11. For the synthesis of 2-halo-1,3-butadienes, see: a) J. Pornet, Tetrahedron Lett. 1981, 22, 453;
12. b) A. Horvát, J.-E. Bäckvall J. Org. Chem. 2001, 66, 8120-8126;
13. c) S. Ma, G. Wang, Tetrahedron Lett. 2002, 43, 5723.
14. For some recent reports of the synthesis of β-chlorostyrenes through the classical Hunsdiecker reaction, see: a) D. Naskar, S. Chowdhury, S. Roy, Tetrahedron Lett. 1998, 39, 699;
15. b) S. C. Roy, C. Guin, G. Maiti, Tetrahedron Lett. 2001, 42, 9253;
16. c) C. Kuang, H. Senboku, M. Tokuda, Synlett 2000, 1439.
17. For the synthesis of α-chlorostyrenes, see: T. J. Barton, G. T. Burns, Organometallics 1982, 1, 1455.
18. A. Minato, K. Suzuki, K. Tamao, J. Am. Chem. Soc. 1987, 109, 1257.
19. a) C. Xu, E. Negishi, Tetrahedron Lett. 1999, 40, 431-434;
20. b) X. Zeng, M. Qian, Q. Hu, E. Negishi, Angew. Chem. Int. Ed. 2004, 43, 2259-2263.
21. a) W. R. Roush, K. J. Moriarty, B. B. Brown, Tetrahedron Lett. 1990, 31, 6509-6512;
22. b) L. S. M. Wong, L. A. Sharp, N. M. C. Xavier, P. Turner, M. S. Sherburn, Org. Lett. 2002, 4, 1995.
23. W. Shen, L. Wang, J. Org. Chem. 1999, 64, 8873-8879.
24. J. Uenishi, K. Matsui, Tetrahedron Lett. 2001, 42, 4353.
25. M. Qian, Z. Huang, E. Negishi Org. Lett. 2004, 6, 1531-1534 and references cited therein.
26. a) M. G. Organ, J. T. Cooper, L. R. Rogers, F. Soleymanzadeh, T. Paul, J. Org. Chem. 2000, 65, 7959-7970;
27. b) H. Gashemi, L. M. Antunes, M. C. Organ, Org. Lett. 2004, 6, 2913-2916.
28. For a review on the applications of 1,2-dichloroethylene in cross-coupling reactions, see: M. Alami, J.-F. Peyrat, J-D. Brion, Synthesis 2000, 11, 1499-1518.
29. M. Mladenova, M. Alami, G. Listrumelle, Tetrahedron Lett. 1996, 37, 6547-6550 and references cited therein.
30. V. Ratovelomanana, G. Listrumelle, Tetrahedron Lett. 1981, 22, 315-318.
31. V. Ratovelomanana, G. Listrumelle, Tetrahedron Lett. 1984, 25, 6001-6004.
32. X. Chen, J. G. Millar, Synthesis 2000, 113-118.
33. V. Ratovelomanana, A. Hammoud, G. Linstrumelle, Tetrahedron Lett. 1987, 28, 1649-50.
34. For recent general reviews on the Suzuki-Miyaura cross-coupling, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
35. b) N. Miyaura, Top. Curr. Chem. 2002, 219, 11.
36. For a recent example of Suzuki-Miyaura couplings with vinyl chlorides, see: A. Littke, C. Dai, G. Fu, J. Am. Chem. Soc. 2000, 122, 4020-4028.
37. For the use of XPhos in Suzuki couplings: H. N. Nguyen, X. Huang, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 11818-11819.
38. a) For Suzuki reactions with DavePhos, see: J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561;
39. b) for Suzuki reactions with S-Phos, see: T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685-4696.
40. Electron-poor arylboronic acids are known to give poor results in Suzuki reactions due to homocoupling and decomposition via deprotoborination processes. In fact, in most of the Suzuki-Miyaura reactions a considerable excess of the boronic acid is used to allow for complete conversion of the coupling reaction. For a recent study on homocoupling reactions of boronic acids see: M. S. Wong, X. L. Zang, Tetrahedron Lett. 2001, 42, 4087-4089.
41. H. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1975, 97, 5249-5255.