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

Ming-Hang Bi; Ying Cheng; Wen-Jing Xiao; Jia-Rong Chen

doi:10.1021/acs.orglett.2c03020

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

Org Lett. 2022 Oct 21;24(41):7589-7594. doi: 10.1021/acs.orglett.2c03020. Epub 2022 Oct 8.

Authors

Ming-Hang Bi¹, Ying Cheng¹, Wen-Jing Xiao^{1

2}, Jia-Rong Chen^{1

3}

Affiliations

¹ 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.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou730000, China.
³ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan453007, China.

PMID: 36208484
DOI: 10.1021/acs.orglett.2c03020

Abstract

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 CF₂-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.