Issue 11, 2024

Expedient deaminative phosphorylation and sulfonylation of benzylic tertiary amines enabled by difluorocarbene

Abstract

Organophosphines and sulfones have a wide range of applications and they are prevalent in bioactive molecules as well as pharmaceutical compounds. Numerous strategies have been developed to synthesize them in modern synthetic chemistry. However, compared with transition metal-catalyzed strategies and photocatalysis-promoted methods, the transition metal-free protocols are elusive and have been less reported. Herein we report a difluorocarbene-enabled deaminative phosphonylation and sulfonylation reaction. Various allylic diphenylphosphine oxides and allylic sulfones could be obtained smoothly from the corresponding benzylic tertiary amines in moderate to high yields via this method.

Graphical abstract: Expedient deaminative phosphorylation and sulfonylation of benzylic tertiary amines enabled by difluorocarbene

Supplementary files

Article information

Article type
Research Article
Submitted
04 Mar 2024
Accepted
14 Apr 2024
First published
16 Apr 2024

Org. Chem. Front., 2024,11, 3179-3185

Expedient deaminative phosphorylation and sulfonylation of benzylic tertiary amines enabled by difluorocarbene

C. Li, Y. Guo, J. Su, X. Hu, Q. Xuan and Q. Song, Org. Chem. Front., 2024, 11, 3179 DOI: 10.1039/D4QO00412D

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