Catalytic regioselective construction of phenylthio- and phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones

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.

Graphical abstract: Catalytic regioselective construction of phenylthio- and phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones

Supplementary files

Article information

Article type
Communication
Submitted
19 Oct 2021
Accepted
23 Nov 2021
First published
25 Nov 2021

Chem. Commun., 2021, Advance Article

Catalytic regioselective construction of phenylthio- and phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones

H. Shi, S. Li, F. Zhang and J. Ma, Chem. Commun., 2021, Advance Article , DOI: 10.1039/D1CC05890H

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