Silver-Promoted Radical Cascade Aryldifluoromethylation/Cyclization of 2-Allyloxybenzaldehydes for the Synthesis of 3-Aryldifluoromethyl-Containing Chroman-4-one Derivatives

Qianqian Sun; Hongxiao Li; Xingyu Chen; Jian Hao; Hongmei Deng; Haizhen Jiang

doi:10.3390/molecules28083578

Silver-Promoted Radical Cascade Aryldifluoromethylation/Cyclization of 2-Allyloxybenzaldehydes for the Synthesis of 3-Aryldifluoromethyl-Containing Chroman-4-one Derivatives

Molecules. 2023 Apr 19;28(8):3578. doi: 10.3390/molecules28083578.

Authors

Qianqian Sun¹, Hongxiao Li¹, Xingyu Chen¹, Jian Hao¹, Hongmei Deng², Haizhen Jiang^{1

3}

Affiliations

¹ Department of Chemistry, Shanghai University, Shanghai 200444, China.
² Laboratory for Microstructures, Shanghai University, Shanghai 200444, China.
³ Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

Abstract

A convenient silver-promoted radical cascade aryldifluoromethylation/cyclization of 2-allyloxybenzaldehydes has been developed. Experimental studies disclosed that the addition of aryldifluoromethyl radicals in situ produced from easily accessible gem-difluoroarylacetic acids to unactivated double bonds in 2-allyloxybenzaldehyde was an effective route to access a series of 3-aryldifluoromethyl-containing chroman-4-one derivatives in moderate to good yields under mild reaction conditions.

Keywords: aryldifluoromethylation/cyclization; chroman-4-one derivatives; radical cascade.

Grants and funding

This research received no external funding.