Three-Component Coupling Reactions of Thioformamides with Organolithium and Grignard Reagents Leading to Formation of Tertiary Amines and a Thiolating Agent

Toshiaki Murai* and Fumio Asai
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan
J. Am. Chem. Soc., 2007, 129 (4), pp 780–781
DOI: 10.1021/ja068523f
Publication Date (Web): January 3, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mtoshi@gifu-u.ac.jp

Abstract

Abstract Image

A highly efficient three-component coupling reaction between thioformamides and organolithium and Grignard reagents was developed. The generality of the process has been demonstrated by using various combinations of reactants and reagents. Information about the mechanism of the reaction has come from 1H and 13C NMR spectroscopic detection of the key intermediate. The LiS group in the intermediates generated by addition of the organolithium reagents to the thioformamides serves as a leaving group. The solid byproduct formed in these reactions, formulated as [LiSMgBr], can be used as a thiolating agent to transform acid chlorides into thioic acids and thioic acid anhydrides.

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History

  • Published In Issue January 31, 2007
  • Received November 28, 2006

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