Issue 12, 2019

Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

Abstract

Classical 1,4-dicarbofunctionalization of 1,3-enynes employs organometallic reagents as nucleophiles to initiate the reaction. We report a copper-catalyzed 1,4-alkylarylation of 1,3-enynes with alkyl diacyl peroxides as masked alkyl electrophiles and aryl boronic acids as nucleophiles, selectively affording structurally diversified tetrasubstituted allenes under mild conditions. Mechanistic studies suggest that an allenyl radical might be involved.

Graphical abstract: Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Dec 2018
Accepted
18 Feb 2019
First published
19 Feb 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3632-3636

Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles

C. Ye, Y. Li, X. Zhu, S. Hu, D. Yuan and H. Bao, Chem. Sci., 2019, 10, 3632 DOI: 10.1039/C8SC05689G

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