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Issue 22, 2015
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Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents

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Abstract

A copper-free allylic arylation reaction between 3,3-disubstituted allylic halides and triazene-softened aryl Grignard reagents has been developed. This protocol presents a direct and efficient way to construct both α- or γ-isomers with high regioselectivity under environmentally benign conditions. Various functional groups can be tolerated in the reaction and the products are of high value for multiple synthetic applications. The α- and γ-isomers can be converted to the corresponding 3H-indole and indole derivatives in multigram scale respectively.

Graphical abstract: Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents

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Supplementary files

Article information


Submitted
25 Mar 2015
Accepted
29 Apr 2015
First published
29 Apr 2015

Org. Biomol. Chem., 2015,13, 6333-6337
Article type
Paper
Author version available

Copper-free arylation of 3,3-disubstituted allylic halides with triazene-softened aryl Grignard reagents

L. Xu, Z. Liu, W. Dong, J. Song, M. Miao, J. Xu and H. Ren, Org. Biomol. Chem., 2015, 13, 6333
DOI: 10.1039/C5OB00594A

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