Issue 17, 2024

Ligand-assisted manganese-enabled direct C–H difluoromethylation of arenes

Abstract

The incorporation of a difluoromethyl group within an aromatic ring is highly desirable. However, studies on direct C–H difluoromethylation reactions of arenes have been sparsely reported in the literature. Therefore, in this work, a light-induced Mn-enabled DavePhos-promoted direct C–H difluoromethylation reaction of general arenes has been explored in detail using ArSO2CF2Br with variable characteristics as the coupling partner under mild conditions. Various arenes and bioactive molecules were all well tolerated, producing the resultant products in moderate to high yields. Preliminary mechanistic studies suggested that Mn2(CO)10 could not only mediate the halogen-atom transfer process (XAT) to provide active ArSO2CF2˙ radicals but also coordinate with the arenes through π-complexation to activate the aromatic ring. This facilitated the reaction between the aromatic ring and the ArSO2CF2˙ radical.

Graphical abstract: Ligand-assisted manganese-enabled direct C–H difluoromethylation of arenes

Supplementary files

Article information

Article type
Research Article
Submitted
02 May 2024
Accepted
06 Jul 2024
First published
10 Jul 2024

Org. Chem. Front., 2024,11, 4874-4881

Ligand-assisted manganese-enabled direct C–H difluoromethylation of arenes

K. Zhou, S. Xia, Y. Xiao, Z. Huang, J. Zhang and Y. Zhao, Org. Chem. Front., 2024, 11, 4874 DOI: 10.1039/D4QO00786G

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