Solvent and Catalyst-Free Mechanochemical C(sp3)–S Cross-Coupling/Cyclization/Dehydration Cascade: Substrate-Controlled Divergent Synthesis of 2,3-Dihydrothiazoles and Thiazolidines

Raghuvanshi, Keshav (2026) Solvent and Catalyst-Free Mechanochemical C(sp3)–S Cross-Coupling/Cyclization/Dehydration Cascade: Substrate-Controlled Divergent Synthesis of 2,3-Dihydrothiazoles and Thiazolidines. The Journal of Organic Chemistry, 91 (24). pp. 8206-8220.

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Official URL: https://doi.org/10.1021/acs.joc.6c00447

Abstract

Mechanochemistry has emerged as a powerful tool for enabling solvent-free, energy-efficient, and sustainable chemical transformation. Herein, we report a mechanochemical strategy for the direct synthesis of 2,3-dihydrothiazoles and thiazolidines employing easily accessible β-ketothioamides and α-bromoketones/1,3-dichloroprop-2-one under solvent-free condition in a mortar and pestle at room temperature within 15 min. The reaction proceeds via consecutive C(sp3)–S cross-coupling/intramolecular cyclization/dehydration cascade affording higher yields compared to solution-based traditional methods, which typically require reaction times of several hours. This process features operationally simple mild condition, short reaction time, chemo-/regioselectivity, broad substrate scope, good functional group compatibility, excellent yields, facile scalability, and overcomes key synthetic challenges. Noteworthy, stereochemistry of the exocyclic double bond was assigned to have Z-configuration.

Item Type:	Article
Uncontrolled Keywords:	Chemical reactions Mechanochemistry Molecular structure Reaction products Thermodynamic properties
Subjects:	Coal Gesification
Divisions:	UNSPECIFIED
Depositing User:	Mr. B. R. Panduranga
Date Deposited:	07 Jul 2026 04:19
Last Modified:	07 Jul 2026 04:19
URI:	https://cimfr.csircentral.net/id/eprint/3033

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