Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones

Zuxiao Zhang; Xiao-Jun Tang; William R Dolbier Jr

doi:10.1021/acs.orglett.6b00168

Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones

Org Lett. 2016 Mar 4;18(5):1048-51. doi: 10.1021/acs.orglett.6b00168. Epub 2016 Feb 11.

Authors

Zuxiao Zhang¹, Xiao-Jun Tang¹, William R Dolbier Jr¹

Affiliation

¹ Department of Chemistry, University of Florida , Gainesville, Florida 32611-7200, United States.

PMID: 26866977
DOI: 10.1021/acs.orglett.6b00168

Abstract

A visible light-mediated difluoromethylation of N-benzylacrylamides with HCF2SO2Cl as the HCF2 radical precursor is described. The reaction incorporates a tandem cyclization/dearomatization process to afford various difluoromethylated 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.