Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system

• DOI: 10.1039/c3sc51209f
• Publication Date: 2013-05-21T15:03:36Z
• Authors: Dale J. Wilger; Nathan J. Gesmundo; David A. Nicewicz
• Keywords: Thiophenol; Alkene; Stoichiometry

Herein is presented a direct method for the metal-free hydrotrifluoromethylation of alkenes. The relies on single electron oxidation commercially available sodium trifluoromethanesulfinate salt (CF3SO2Na, Langlois reagent) by N-Me-9-mesityl acridinium as photoredox catalyst. Methyl thiosalicylate used substoichiometric H-atom donor aliphatic alkenes, and thiophenol stoichiometric styrenyl substrates. substrate scope transformation broad, including mono-, di- trisubstituted with high regioselectivity in nearly all cases examined.