Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2 H-Chromenes

Nengneng Zhou; Ziqin Xia; Kaimo Kuang; Qiankun Xu; Fangli Zhao; Lei Wang; Man Zhang

doi:10.1021/acs.orglett.2c02314

Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2 H-Chromenes

Org Lett. 2022 Aug 12;24(31):5791-5796. doi: 10.1021/acs.orglett.2c02314. Epub 2022 Aug 2.

Authors

Nengneng Zhou¹, Ziqin Xia¹, Kaimo Kuang¹, Qiankun Xu¹, Fangli Zhao¹, Lei Wang¹, Man Zhang¹

Affiliation

¹ Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.

PMID: 35916599
DOI: 10.1021/acs.orglett.2c02314

Abstract

A novel visible-light-mediated difluoroalkylation of 1-(allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-arylvinyl)-2-(vinyloxy)benzenes for the synthesis of bis-difluoroalkylated benzoxepines and 2H-chromenes is developed. This method features mild reaction conditions, good regioselectivity, a wide substrate scope, good functional-group compatibility, and late-stage modification. Preliminary mechanistic studies reveal that the generation of the CF₂CO₂Et radical is more prone to reaction with the double bond of the aryl group.