Metal-Free Highly Regioselective 1,4-Sulfonyliodination of 1,3-Enynes

Herein, a novel, practical, and green synthetic method using readily available 1,3-enynes with sulfonyl hydrazides and I2 through tert-butyl hydroperoxide (TBHP)-mediated 1,4-sulfonyliodination has been developed for synthesizing various tetrasubstituted allenyl iodides under metal-free conditions....

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Bibliographic Details
Published in:Journal of organic chemistry 2023-02, Vol.88 (4), p.2034-2045
Main Authors: Lv, Yunhe, Lai, Junrong, Pu, Weiya, Wang, Jin, Han, Wanru, Wang, Axue, Zhang, Mengyue, Wang, Xue
Format: Article
Language:English
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Summary:Herein, a novel, practical, and green synthetic method using readily available 1,3-enynes with sulfonyl hydrazides and I2 through tert-butyl hydroperoxide (TBHP)-mediated 1,4-sulfonyliodination has been developed for synthesizing various tetrasubstituted allenyl iodides under metal-free conditions. Notably, the proposed method exhibits a broad substrate scope, operational simplicity, tolerance to air, high functional-group tolerance, satisfactory yields, and excellent regioselectivity as well as involves the use of cost-effective reagents such as green oxidants.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02257