Catalytic generation and selective heterocoupling of two electron-rich alkenes

Angewandte Chemie - International Edition

Volumn 52, Issue 23, 2013, Pages 6038-6042

  Galván, Alicia ^a   Calleja, Jonás ^a   Fañanás, Francisco J ^a   Rodríguez, Félix ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

cascade reactions; cyclization; heterocycles; homogeneous catalysis; platinum

Indexed keywords

ALKYNOLS; CASCADE REACTIONS; CYCLOISOMERIZATIONS; ELECTRON-RICH ALKENES; HETEROCYCLES; HOMOGENEOUS CATALYSIS; STEREOCENTERS;

HYDROCARBONS; PLATINUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

EID: 84878423210     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209870     Document Type: Article

References (22)

1. L. J. Gooßen, N. Rodríguez, Angew. Chem. 2007, 119, 7688-7690
2. Angew. Chem. Int. Ed. 2007, 46, 7544-7546.
3. Y. Yamamoto, Chem. Rev. 2012, 112, 4736-4769.
4. The Mukaiyama-Michael addition and related reactions could be seen as heterocoupling reactions of two different alkenes. The different electronic nature of the alkenes involved in this reaction (poor and rich) make this process a special case of heterocoupling reactions of alkenes. We consider that the coupling reactions involving unbiased alkenes or the coupling of two electron-rich (or two electron-poor) alkenes are more appealing processes. For a review on the Mukaiyama-Michael reaction, see: Comprehensive Asymmetric Catalysis (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, New York, 1999, chap. 31.
5. P. W. Jolly, G. Wilke, in Applied Homogeneous Catalysis with Organometallic Compounds, Vol.3, 2 nd ed., (Eds.: B. Cornils, W.A. Herrmann,), Wiley-VCH, Weinheim, 2002, pp. 1164-1189.
6. T. V. RajanBabu, Chem. Rev. 2003, 103, 2845-2860.
7. 3, see:, J. Dai, J. Wu, G. Zhao, W.-M. Dai, Chem. Eur. J. 2011, 17, 8290-8293.
8. Y. Ura, H. Tsujita, K. Wada, T. Kondo, T. Mitsudo, J. Org. Chem. 2005, 70, 6623-6628.
9. H. Tsujita, Y. Ura, S. Matsuki, K. Wada, T. Mitsudo, T. Kondo, Angew. Chem. 2007, 119, 5252-5255
10. Angew. Chem. Int. Ed. 2007, 46, 5160-5163.
11. J. Barluenga, L. Alvarez-Rodrigo, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2004, 116, 4022-4025
12. Angew. Chem. Int. Ed. 2004, 43, 3932-3935
13. J. Barluenga, L. Alvarez-Rodrigo, F. Rodríguez, F. J. Fañanás, Angew. Chem. 2006, 118, 6510-6513
14. Angew. Chem. Int. Ed. 2006, 45, 6362-6365
15. J. Barluenga, L. Alvarez-Rodrigo, F. Rodríguez, F. J. Fañanás, T. L. Sordo, P. Campomanes, Angew. Chem. 2007, 119, 2661-2663
16. Angew. Chem. Int. Ed. 2007, 46, 2607-2609.
17. C. Agami, F. Couty, Tetrahedron 2002, 58, 2701-2724.
18. CCDC910137 (3 h) and 923744 (6 b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
19. T. G. Driver, T. J. Williams, J. A. Labinger, J. E. Bercaw, Organometallics 2007, 26, 294
20. R. Romco, G. D'Amico, Organometallics 2006, 25, 3435
21. B. L. Bennett, J. M. Hoerter, J. F. Houlis, D. M. Roddick, Organometallics 2000, 19, 615.
22. B. Maji, S. Lakhdar, H. Mayr, Chem. Eur. J. 2012, 18, 5732-5740.