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Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.
J Am Chem Soc 2011; 133(47):19020-3JA

Abstract

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.

Authors+Show Affiliations

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22066899

Citation

Matsubara, Ryosuke, et al. "Nickel-catalyzed Heck-type Reactions of Benzyl Chlorides and Simple Olefins." Journal of the American Chemical Society, vol. 133, no. 47, 2011, pp. 19020-3.
Matsubara R, Gutierrez AC, Jamison TF. Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins. J Am Chem Soc. 2011;133(47):19020-3.
Matsubara, R., Gutierrez, A. C., & Jamison, T. F. (2011). Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins. Journal of the American Chemical Society, 133(47), pp. 19020-3. doi:10.1021/ja209235d.
Matsubara R, Gutierrez AC, Jamison TF. Nickel-catalyzed Heck-type Reactions of Benzyl Chlorides and Simple Olefins. J Am Chem Soc. 2011 Nov 30;133(47):19020-3. PubMed PMID: 22066899.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins. AU - Matsubara,Ryosuke, AU - Gutierrez,Alicia C, AU - Jamison,Timothy F, Y1 - 2011/11/08/ PY - 2011/11/10/entrez PY - 2011/11/10/pubmed PY - 2012/3/21/medline SP - 19020 EP - 3 JF - Journal of the American Chemical Society JO - J. Am. Chem. Soc. VL - 133 IS - 47 N2 - 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. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/22066899/Nickel_catalyzed_Heck_type_reactions_of_benzyl_chlorides_and_simple_olefins_ L2 - https://dx.doi.org/10.1021/ja209235d DB - PRIME DP - Unbound Medicine ER -