K2S2O8-Mediated Selective Trifluoromethylacylation and Trifluoromethylarylation of Alkenes under Transition-Metal-Free Conditions: Synthetic Scope and Mechanistic Studies

• DOI: 10.1021/acs.orglett.8b02846
• Publication Date: 2018-10-05T14:31:11Z
• Authors: Lin Tang; Zhen Yang; Xueping Chang; Jingchao Jiao; Xiantao Ma; Weihao Rao; Qiuju Zhou; Lingyun Zheng
• Keywords: Scope (computer science); Aqueous medium

A practical and efficient method for selective intramolecular radical trifluoromethylacylation -arylation of alkenes with inexpensive CF3SO2Na K2S2O8 in aqueous media has been developed, respectively, affording the highly chemoselective synthesis CF3-functionalized chroman-4-ones chromanes satisfactory yields. Control experiments DFT calculations indicate that CF3SO2Na/K2S2O8 system is capable trifluoromethylating substrate without a transition metal catalyst oxidation to ·CF3 by involved rate-determining step.