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(Trifluoromethyl)thiolation of 2‐Alkynylbenzoates: An Efficient Route to 4‐[(Trifluoromethyl)thio]‐1 H ‐isochromen‐1‐ones
Author(s) -
Li Yuewen,
Li Guangming,
Ding Qiuping
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402629
Subject(s) - trifluoromethyl , chemistry , thio , electrophile , isocoumarin , lewis acids and bases , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl
The incorporation of the (trifluoromethyl)thio group into the isocoumarin scaffold through a Lewis‐acid‐mediated electrophilic cyclization reaction of 2‐(2‐alkynyl)benzoates with trifluoromethanesulfanylamide is reported. The transformation proceeds well in the presence of BiCl 3 and BF 3 · Et 2 O under mild conditions to give 4‐[(trifluoromethyl)thio]‐1 H ‐isochromen‐1‐ones regioselectively and in good yields.