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Indium-Catalyzed Reductive Dithioacetalization of Carboxylic Acids with Dithiols: Scope, Limitations, and Application to Oxidative Desulfurization

Author:
Nishino, Kota, Minato, Kohei, Miyazaki, Takahiro, Ogiwara, Yohei, Sakai, Norio
Source:
Journal of organic chemistry 2017 v.82 no.7 pp. 3659-3665
ISSN:
1520-6904
Subject:
aldehydes, carboxylic acids, catalysts, chemical reactions, chemical structure, desulfurization, indium, organic chemistry
Abstract:
In this study an InI₃-TMDS (1,1,3,3-tetramethyldisiloxane) reducing system effectively catalyzed the reductive dithioacetalization of a variety of aromatic and aliphatic carboxylic acids with 1,2-ethanedithiol or 1,3-propanedithiol leading to the one-pot preparation of either 1,3-dithiolane derivatives or a 1,3-dithiane derivative. Also, the intact indium catalyst continuously catalyzed the subsequent oxidative desulfurization of an in situ formed 1,3-dithiolane derivative, which led to the preparation of the corresponding aldehydes.
Agid:
5662498