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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

Saradhi Kalari, Uttam B. Karale, Haridas B. Rode

2022The Journal of Organic Chemistry24 citationsDOI

Abstract

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.

Topics & Concepts

ChemistrySynthonSelectfluorArylOrganic chemistryMedicinal chemistryAlkyneAlkylCatalysisSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions
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 | Litcius