Free-Radical Carbo-Alkenylation of Olefins: Scope, Limitations and Mechanistic Insights.

Chemistry

Institute of Molecular Sciences, UMR-CNRS 5255, University of Bordeaux, 351, Cours de la libération, 33405, Talence cedex, France.

Published: February 2017

The three-component free-radical carbo-alkenylation of electron-rich olefins has been studied, varying the substitution pattern in the alkene, in the radical precursor and in the final acceptor. New vinylsulfones were also prepared and their reactivity investigated. The scope and limitations of the process was established, and the reaction mechanism clarified using selected dienes as radical clocks. It was thus recognised that the reversible addition onto the olefin of the released sulfonyl group is an important event, which should not be overlooked when using such multicomponent carbo-alkenylation reactions.

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http://dx.doi.org/10.1002/chem.201605043DOI Listing

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