Alkene Oxyalkylation Enabled by Merging Rhenium Catalysis with Hypervalent Iodine(III) Reagents via Decarboxylation

Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-12, Vol.135 (48), p.18048-18051
Main Authors: Wang, Yin, Zhang, Lei, Yang, Yunhui, Zhang, Ping, Du, Zhenting, Wang, Congyang
Format: Article
Language:English
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Summary:Rhenium-catalyzed oxyalkylation of alkenes is described, where hypervalent iodine(III) reagents derived from widely occurring aliphatic carboxylic acids were used as, for the first time, not only an oxygenation source but also an alkylation source via decarboxylation. The reaction also features a wide substrate scope, totally regiospecific difunctionalization, mild reaction conditions, and ready availability of both substrates. Mechanistic studies revealed a decarboxylation/radical-addition/cation-trapping cascade operating in the reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja410195j