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A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating α-(het)aroyl-α-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular O-arylation,… Click to show full abstract
A one-pot synthesis of 2-(het)aryl/alkyl-3-cyanobenzofurans has been reported. The overall sequence involves base-induced reaction of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles with benzyl carbamate, generating α-(het)aroyl-α-(2-bromoaryl)acetonitriles, which are in situ subjected to copper-catalyzed intramolecular O-arylation, furnishing the 2-(het)aryl/alkyl-3-cyanobenzofurans in high yields. A probable mechanism for the base-induced cleavage of 2-(2-bromoaryl)-3-(het)aryl-3-(methylthio)acrylonitriles to α-(het)aroyl-α-(2-bromoaryl)acetonitriles in the presence of benzyl carbamate has been proposed.
Journal Title: ACS Omega
Year Published: 2018
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