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Issue 23, 2018
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Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

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Abstract

A nickel-catalyzed conjunctive cross-coupling of non-conjugated alkenes, alkyl halides, and alkylzinc reagents is reported. Regioselectivity is controlled by chelation of a removable bidentate 8-aminoquinoline directing group. Under optimized conditions, a wide range of 1,2-dialkylated products can be accessed in moderate to excellent yields. To the best of our knowledge, this report represents the first example of three-component 1,2-dialkylation of non-conjugated alkenes to introduce differentiated alkyl fragments.

Graphical abstract: Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

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Supplementary files

Article information


Submitted
17 Apr 2018
Accepted
09 May 2018
First published
16 May 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 5278-5283
Article type
Edge Article

Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds

J. Derosa, V. A. van der Puyl, V. T. Tran, M. Liu and Keary M. Engle, Chem. Sci., 2018, 9, 5278
DOI: 10.1039/C8SC01735B

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