Highly selective and robust palladium-catalyzed carbon-carbon coupling between allyl alcohols and aldehydes via transient allylboronic acids

European Journal of Organic Chemistry

Volumn , Issue 18, 2006, Pages 4085-4087

  Selander, Nicklas ^a   Sebelius, Sara ^a   Estay, Cesar ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Aldehydes; Allylation; Boron; Electrophilic substitution; Palladium

Indexed keywords

EID: 33748798754     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600530     Document Type: Article

References (17)

1. a) Y. Tamaru, Eur. J. Org. Chem. 2005, 2647;
2. b) J. Muzart, Tetrahedron 2005, 61, 4179.
3. a) J. P. Takahara, Y. Masuyama, Y. Kurusu, J. Am. Chem. Soc. 1992, 114, 2577;
4. b) M. Kimura, T. Tomizawa, Y Horino, S. Tanaka, Y. Tamaru, Tetrahedron Lett. 2000, 41, 3627;
5. c) M. Kimura, M. Shimizu, K. Shibata, M. Tazoe, Y Tamaru, Angew. Chem. Int. Ed. 2003, 42, 3392;
6. d) S. Araki, T. Kamei, T. Hirashita, H. Yamamura, M. Kawai, Org. Lett. 2000, 2, 847;
7. e) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207;
8. f) J. A. Marshall, Chem. Rev. 2000, 100, 3163;
9. g) S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763;
10. h) Q. Yao, E. P. Kinney, C. Zheng, Org. Lett. 2004, 6, 2997.
11. a) V. J. Olsson, S. Sebelius, N. Selander, K. J. Szabó, J. Am. Chem. Soc. 2006, 128, 4588;
12. b) S. Sebelius, V. J. Olsson, K. J. Szabó, J. Am. Chem. Soc. 2005, 127, 10478.
13. R. W. Hoffmann, Angew. Chem. Int. Ed. Engl. 1982, 21, 555.
14. a) D. G. Hall, Boronic Acids, Wiley, Weinheim, 2005;
15. b) S. Sebelius, O. A. Wallner, K. J. Szabó, Org. Lett. 2003, 5, 3065;
16. c) S. H. Yu, M. J. Ferguson, R. McDonald, D. G. Hall, J. Am. Chem. Soc. 2005, 127, 12808;
17. d) V. Rauniyar, D. G. Hall, Angew. Chem. Int. Ed. 2006, 45, 2426.