Issue 4, 2022

Metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide via cleavage of S–N bonds: expeditious synthesis of diarylsulfones

Abstract

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S–N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated.

Graphical abstract: Metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide via cleavage of S–N bonds: expeditious synthesis of diarylsulfones

Supplementary files

Article information

Article type
Communication
Submitted
11 Nov 2021
Accepted
15 Dec 2021
First published
17 Dec 2021

Org. Biomol. Chem., 2022,20, 768-772

Metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide via cleavage of S–N bonds: expeditious synthesis of diarylsulfones

X. Zhang, Y. Feng, Y. Tuo and Q. Zheng, Org. Biomol. Chem., 2022, 20, 768 DOI: 10.1039/D1OB02209A

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