Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4 H-pyrans

Chun-Yan Wu; Xiang-Long Chen; Dong-Sheng Yang; Yong-Xing Tang; Li-Sheng Wang; Yong-Dong Du; Yan-Dong Wu; An-Xin Wu

doi:10.1021/acs.orglett.4c03266

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4 H-pyrans

Org Lett. 2024 Oct 11;26(40):8589-8593. doi: 10.1021/acs.orglett.4c03266. Epub 2024 Sep 27.

Authors

Chun-Yan Wu¹, Xiang-Long Chen¹, Dong-Sheng Yang¹, Yong-Xing Tang¹, Li-Sheng Wang¹, Yong-Dong Du¹, Yan-Dong Wu¹, An-Xin Wu^{1

2}

Affiliations

¹ State Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China.
² State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

PMID: 39329447
DOI: 10.1021/acs.orglett.4c03266

Abstract

A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4H-pyrans using β-CF₃-1,3-enynes, BrCF₂CO₂Et, and sulfoxonium ylides as readily available substrates has been developed. This metal-free process involves two C-F bond cleavages of β-CF₃-1,3-enynes and a CF₃ group generated in situ from BrCF₂CO₂Et. This method is applicable to the late-stage modification of pharmaceutically active molecules.