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Issue 12, 2014

Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle

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Abstract

A protocol for palladium-catalyzed ortho C(sp2)–H alkenylation via a rarely reported seven-membered palladacycle with oxalyl amide as a directing group was reported. The range of olefins was the broadest yet reported for this kind of C–H alkenylation reaction. For example, allyl acetate, allyl alcohol derivatives, acraldehyde, acrylate and acrylonitrile were all tolerated in this C–H transformation. Sequential alkenylation reactions were also achieved to construct the complex olefinated arenes in good yields in one pot.

Graphical abstract: Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle

Supplementary files

Article information


Submitted
22 Jul 2014
Accepted
20 Aug 2014
First published
20 Aug 2014

Chem. Sci., 2014,5, 4962-4967
Article type
Edge Article

Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle

Q. Wang, J. Han, C. Wang, J. Zhang, Z. Huang, D. Shi and Y. Zhao, Chem. Sci., 2014, 5, 4962 DOI: 10.1039/C4SC02172J

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