Oxalates as Activating Groups for Tertiary Alcohols in Photoredox-Catalyzed gem-Difluoroallylation To Construct All-Carbon Quaternary Centers

Construction of challenging and important all-carbon quaternary centers has received growing attention. Herein, with oxalates as activating groups for tertiary alcohols, we report photoredox-catalyzed gem-difluoroallylation to construct all-carbon quaternary centers enabled by efficient tertiary rad...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2022-06, Vol.87 (12), p.8237-8247
Main Authors: Wang, Qing, Yue, Ling, Bao, Yanyang, Wang, Yanan, Kang, Danni, Gao, Yan, Yuan, Zheliang
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Construction of challenging and important all-carbon quaternary centers has received growing attention. Herein, with oxalates as activating groups for tertiary alcohols, we report photoredox-catalyzed gem-difluoroallylation to construct all-carbon quaternary centers enabled by efficient tertiary radical addition to α-trifluoromethyl alkenes. This transformation shows good functional group tolerance for both α-trifluoromethyl alkenes and oxalates. Moreover, this strategy is also successfully applied to the synthesis of monofluoralkenes from the corresponding electron-rich gem-difluoroalkenes and cesium tertiary alkyl oxalates under modified conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00664