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Issue 38, 2015
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Catalyst-controlled reverse selectivity in C–C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents

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Abstract

An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented. The use of N-heterocyclic carbenes as ligands is key to reverse the common γ-selectivity of this transformation and gives rise to the corresponding linear products with high levels of regioselectivity.

Graphical abstract: Catalyst-controlled reverse selectivity in C–C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents

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Publication details

The article was received on 18 Feb 2015, accepted on 09 Apr 2015 and first published on 09 Apr 2015


Article type: Communication
DOI: 10.1039/C5CC01521A
Chem. Commun., 2015,51, 8142-8145

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    Catalyst-controlled reverse selectivity in C–C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagents

    S. F. Pizzolato, M. Giannerini, P. H. Bos, M. Fañanás-Mastral and B. L. Feringa, Chem. Commun., 2015, 51, 8142
    DOI: 10.1039/C5CC01521A

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