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Selectfluor-Mediated Synthesis of β‑Acyl Allyl Sulfones/β-Acyl Allyl Benzotriazoles from Ketones/Acetylenes, Aryl Sulfinates/Benzotriazole, and DMSO as a Dual-Carbon Synthon

A Selectfluor-mediated approach for the synthesis of β-acyl allyl sulfones/β-acyl allyl benzotriazoles with excellent atom economy from readily available acetophenones/aryl acetylenes, aryl sulfinates/benzotriazoles, and dimethyl sulfoxide (DMSO) is described. In this protocol, DMSO acts as a dual-c...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-03, Vol.87 (5), p.2435-2445
Main Authors: Kalari, Saradhi, Karale, Uttam B, Rode, Haridas B
Format: Article
Language:English
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Summary:A Selectfluor-mediated approach for the synthesis of β-acyl allyl sulfones/β-acyl allyl benzotriazoles with excellent atom economy from readily available acetophenones/aryl acetylenes, aryl sulfinates/benzotriazoles, and dimethyl sulfoxide (DMSO) is described. In this protocol, DMSO acts as a dual-carbon synthon, resulting in a transition-metal-free construction of two C–C and one C–S or two C–C and one C–N bonds in one pot. This approach is extended to generate chemically diverse compounds. Additionally, β-acyl allyl sulfones/β-acyl allyl benzotriazoles were prepared from acetylenes instead of acetophenones.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02348