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 (free Supporting Information)
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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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