Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4<i>H</i>-pyrans
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang, Yong‐Xing Tang, Lisheng Wang, Yong-Dong Du, Yan‐Dong Wu, An‐Xin Wu
Abstract
A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4 H -pyrans using β-CF 3 -1,3-enynes, BrCF 2 CO 2 Et, and sulfoxonium ylides as readily available substrates has been developed. This metal-free process involves two C–F bond cleavages of β-CF 3 -1,3-enynes and a CF 3 group generated in situ from BrCF 2 CO 2 Et. This method is applicable to the late-stage modification of pharmaceutically active molecules.
Topics & Concepts
DifluorocarbeneTrifluoromethylationChemistryTrifluoromethylOrganic chemistryMedicinal chemistryCombinatorial chemistryStereochemistryAlkylFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsSynthesis and Biological Evaluation