Visible-Light-Induced Photoredox-Catalyzed Selective 1,4-Difluoroalkylesterification of 1-Aryl-1,3-dienes.

Org Lett

CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei430079, China.

Published: October 2022

A selective three-component 1,4-difluoroalkylesterification of 1-aryl-1,3-dienes enabled by dual photoredox and copper catalysis is described. This protocol uses commercially available CF-reagents as radical precursors and carboxylic acids as oxygen-based nucleophiles, providing access to difluoroalkylated allylic esters. This protocol could be extended to intramolecular two-component 1,4-difluoroalkylesterification to access 3-substituted benzobutyrolactones. Preliminary mechanistic studies support a radical process.

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http://dx.doi.org/10.1021/acs.orglett.2c03020DOI Listing

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