Free radical carbochloromethylations
of ortho-cyanoarylacrylamides and N-(arylsulfonyl)acrylamides
have been developed by employing simple alkyl chlorides as the chloromethyl
source. The transformations are characterized by wide functional group
compatibility and utilizing readily available reagents, thus providing
efficient methods for constructing polychloromethyl-substituted quinoline-2,4-diones
and α-aryl-β-polychloromethylated amides.
An oxidative azido-difluoromethylthiolation of alkenes
by employing
TMSN3 as the azide source and PhSO2SCF2H as the difluoromethylthiolation reagent is reported. The present
method is characterized by good functional group tolerance, broad
substrate scope, and short reaction time, thereby providing an efficient
access to synthetically useful β-difluoromethylthiolated azides.
Mechanistic studies indicate a radical pathway involved in the reaction.
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