Radical-mediated Ester Group Migration for 1,2,3-Trifunctionalization of Allyl Benzoates

Abstract

Unactivated alkenes are normally regarded as unfavorable substrates in radical transformations, due to the lack of p-π conjugation that efficiently stabilizes radical intermediates. Functional group migration presents a robust strategy for radical difunctionalization of unactivated alkenes, and has made a great progress over the past few decades. However, the migration of ester group has been relatively less investigated. Herein, we disclose a copper-catalyzed ester group migration to unactivated alkene, applied for 1,2,3-trifunctionalization of allyl benzoates. A variety of α,α-difluoro-γ-hydroxy aliphatic esters are readily obtained.

Keywords

Radical reaction / Functional group migration / Ester migration / Alkene functionalization / Copper catalysis

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RIGHTS & PERMISSIONS

Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH