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

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 fro...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 4; pp. 780 - 781
Main Authors Murai, Toshiaki, Asai, Fumio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.01.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
THIOIMINIUM SALTS
ALCOHOLS
SUBSTITUTION
HYDROXYL-GROUPS
ALDEHYDE
DIHALIDES
PROPARGYLAMINES
INHIBITORS
DERIVATIVES
ALKYNE
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Summary: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.
Bibliography:istex:C8EA3BAFD3B3397C4A284280804D163E2BE242C6
ark:/67375/TPS-SZBJ0RK4-B
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja068523f