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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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Article information


Submitted
18 Feb 2015
Accepted
09 Apr 2015
First published
09 Apr 2015

Chem. Commun., 2015,51, 8142-8145
Article type
Communication

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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