Issue 94, 2021

Brønsted acid-catalyzed solvent-controlled regioselective hydrothiolation and diastereoselective cascade cyclization of dienes

Abstract

A highly regio- and diastereo-selective Brønsted acid-catalyzed tandem hydrothiolation/Friedel-Crafts reaction of linear 1,3-dienes has been developed for the first time, which provides a metal-free and atom-economic way of constructing thiochromane derivatives. Meanwhile, by changing the solvent, 4,3-addition hydrothiolation of 1,3-dienes was also discovered. The origin of the observed selectivity was explained by density functional theory calculations.

Graphical abstract: Brønsted acid-catalyzed solvent-controlled regioselective hydrothiolation and diastereoselective cascade cyclization of dienes

Supplementary files

Article information

Article type
Communication
Submitted
24 Sep 2021
Accepted
03 Nov 2021
First published
04 Nov 2021

Chem. Commun., 2021,57, 12639-12642

Brønsted acid-catalyzed solvent-controlled regioselective hydrothiolation and diastereoselective cascade cyclization of dienes

K. Ji, K. Lu, J. Huang, Z. Li, T. Ding and Z. Chen, Chem. Commun., 2021, 57, 12639 DOI: 10.1039/D1CC05383C

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