Sustainable Sulfonylation and Sulfenylation of Indoles with Thiols through Hexamolybdate/HO-Mediated Oxidative Dehydrogenation Coupling.

J Org Chem

Key Lab of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.

Published: March 2025

Arylsulfonylindole and arylsulfenylindole motifs stand as privileged scaffolds in drug discovery. Traditional methods for synthesizing these molecules have relied mainly on prefunctionalized precursors, involving multistep processes and generating a large amount of waste. In this study, we present a modular protocol for the preparation of 3-sulfonylindoles and 3-sulfenylindoles using indoles and thiols as starting materials via hexamolybdate/HO-mediated oxidative dehydrogenative C-S coupling. Notably, this method features a simple reaction setup and uses readily available thiols as a sulfide source, HO as a green oxidant and oxygen source, alcohol as solvent, recyclable hexamolybdate as a catalyst, and water as the sole byproduct. These metrics are an acceptable green organic synthesis process.

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http://dx.doi.org/10.1021/acs.joc.4c03099DOI Listing

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