Sequential Addition Reactions of Two Molecules of Grignard Reagents to Thioformamides

Toshiaki Murai*, Kazuki Ui and Narengerile

*Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan, Email: mtoshigifu-u.ac.jp

T. Murai, K. Ui, Narengerile, J. Org. Chem., 2009, 74, 5703-5706.

DOI: 10.1021/jo900915n

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Abstract

Sequential addition reactions of Grignard reagents to thioformamides give tertiary amines in an efficient manner. The addition of different Grignard reagents can be accomplished by using one equivalent of arylmagnesium reagent in the first step followed by alkyl, alkenyl, aryl, or alkynyl reagents to afford the corresponding amines in good to high yields.

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

T. Murai, F. Asai, J. Am. Chem. Soc., 2007, 129, 780-781.

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Key Words

Benzylamines (Arylation, Alkylation), Grignard Reagents

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ID: J42-Y2009-2430