SCHEDULED MAINTENANCE
Catalytic regioselective construction of phenylthio- and phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones†
Fa-Guang
Zhang 
*ab
and
Jun-An
Ma
*ab
*ab
and
Jun-An
Ma
*ab
Abstract
Here we report the design and synthesis of two new difluoro-diazoketone reagents (difluorophenylthiol diazoketone and difluorophenoxyl diazoketone) and their [3+2] cycloaddition reactions with aryldiazonium salts under silver catalysis conditions. This protocol enables regioselective access to a broad scope of difluorophenylthiol- and difluorophenoxyl-substituted tetrazole-carbinols in a one-pot operation. Further synthetic derivatizations including dephenylthiolation and unexpected phenylthiol group migration/fluorination allow the efficient preparation of α-difluoromethyl tetrazole-carbinols and α-trifluoromethyl tetrazole-thioethers.
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