Mild and Catalyst-Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N-Benzyl Propargylamines

Huangdi Feng, Huihui Jia and Zhihua Sun*

*College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai 201620, China, Email: sungarisgmail.com

H. Feng, H. Jia, Z. Sun, J. Org. Chem., 2014, 79, 11812-11818.

DOI: 10.1021/jo502349a

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Abstract

A one-pot catalyst-free chemoselective synthesis of N-benzyl propargylamines with good functional group compatibility involves in situ formation of an active amine through Petasis reaction of primary amines, formaldehyde solution, and boronic acids, which reacts in a decarboxylative coupling reaction with propiolic acids to give products in high yields.

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Key Words

Petasis Reaction, Benzylamines, Propargylamines, Multicomponent Reactions

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ID: J42-Y2014