Issue 2, 2025

Brønsted acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols

Abstract

A novel p-toluenesulfonic acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols for the efficient and chemoselective preparation of densely functionalized furan- and lactone-based sulfides under mild metal-free conditions has been developed. By using thiols as nucleophiles in DCE at 80 °C, a new reactivity involving a cascade C5-selective nucleophilic substitution/protonation–hydration/C–S bond cleavage/thia-Michael addition reaction leading to lactone-based sulfides rather than the known Piancatelli-type rearrangement products was revealed for the first time. This tunable thiolation protocol enables ready access to both furan- and lactone-based sulfide derivatives with excellent yields by the judicious choice of the reaction solvent.

Graphical abstract: Brønsted acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols

Supplementary files

Article information

Article type
Research Article
Submitted
10 Oct 2024
Accepted
15 Nov 2024
First published
20 Nov 2024

Org. Chem. Front., 2025,12, 678-683

Brønsted acid-catalyzed solvent-controlled regioselective thiolation of 2-furylcarbinols

C. Zhang, T. Lin, Q. Liu, R. Hu and W. Rao, Org. Chem. Front., 2025, 12, 678 DOI: 10.1039/D4QO01904K

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