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

Kota Nishino; Kohei Minato; Takahiro Miyazaki; Yohei Ogiwara; Norio Sakai

doi:10.1021/acs.joc.7b00170

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

J Org Chem. 2017 Apr 7;82(7):3659-3665. doi: 10.1021/acs.joc.7b00170. Epub 2017 Mar 27.

Authors

Kota Nishino¹, Kohei Minato¹, Takahiro Miyazaki¹, Yohei Ogiwara¹, Norio Sakai¹

Affiliation

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI) , Noda, Chiba 278-8510, Japan.

PMID: 28322050
DOI: 10.1021/acs.joc.7b00170

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.

Publication types

Research Support, Non-U.S. Gov't