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Manganese‐Dioxide‐Catalyzed Trifluoromethylation and Azidation of Styrenyl Olefins via Radical Intermediates
Author(s) -
Panday Prabhakar,
Garg Parul,
Singh Anand
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700508
Subject(s) - chemistry , trifluoromethylation , enol , reagent , manganese , catalysis , organic chemistry , ketone , trifluoromethyl , azide , alkyl
A manganese‐dioxide‐catalyzed trifluoromethylation of styrenes and enol acetates using the Langlois reagent is reported. Employing oxygen/air as the oxidant, styrenes afforded a mixture of the trifluoromethylacohol and ketone products in good overall yields. The protocol also works successfully for converting α‐methylstyrene derivatives to the corresponding trifluoromethyl alcohols. The keto‐trifluoromethylated products could be obtained exclusively when using enol acetates as substrates under the same reaction conditions. The method was extended to the radical azidation of enol acetates using trimethylsilyl azide to furnish the corresponding azido‐ketones in good yields.