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General sulfone construction via sulfur dioxide surrogate control

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Abstract

A highly efficient one-step synthesis of alkyl–alkyl and aryl–alkyl sulfones with a facile combination of halides, sulfur dioxide surrogates and phosphate esters is described. When thiourea dioxide was employed as a reductive sulfur dioxide surrogate, alkyl–alkyl sulfones were obtained under transition metal free conditions. Aryl–alkyl sulfones were obtained with an extremely low catalytic loading (0.2 mol%) via altering the mask of sulfur dioxide surrogates to sodium dithionite. A phosphate ester was employed as a stable and readily available alkyl source. Notably, this protocol has been applied to the late-stage modification of natural products and bioactive molecules.

Graphical abstract: General sulfone construction via sulfur dioxide surrogate control

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Article information


Submitted
08 Nov 2019
Accepted
05 Dec 2019
First published
05 Dec 2019

Green Chem., 2020, Advance Article
Article type
Communication

General sulfone construction via sulfur dioxide surrogate control

S. Chen, Y. Li, M. Wang and X. Jiang, Green Chem., 2020, Advance Article , DOI: 10.1039/C9GC03841H

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