Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins
Author(s)
Matsubara, Ryosuke; Gutierrez, Alicia C.; Jamison, Timothy F.![Thumbnail](/bitstream/handle/1721.1/76192/ACG%20TFJ%20Org%20Lett%202011.pdf.jpg?sequence=6&isAllowed=y)
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Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity.
Date issued
2011-11Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Matsubara, Ryosuke, Alicia C. Gutierrez, and Timothy F. Jamison. “Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins.” Journal of the American Chemical Society 133.47 (2011): 19020–19023.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126