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Issue 5, 2018
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Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

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Abstract

Although chelation-assisted C–H olefination has been intensely investigated, Pd(II)-catalyzed C–H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd(II)-catalyzed olefination of the C(sp2)–H bond with simple aliphatic alkenes using a weakly coordinating monodentate amide auxiliary. Oxygen is used as the terminal oxidant with catalytic copper as the co-oxidant. A variety of functional groups in the aliphatic alkenes are tolerated. Upon hydrogenation, the ortho-alkylated product can be accessed. The utility of this reaction is also demonstrated by the late-stage diversification of drug molecules.

Graphical abstract: Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

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Supplementary files

Article information


Submitted
08 Nov 2017
Accepted
08 Dec 2017
First published
08 Dec 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 1311-1316
Article type
Edge Article

Ligand-enabled ortho-C–H olefination of phenylacetic amides with unactivated alkenes

M. Lu, X. Chen, H. Xu, H. Dai and J. Yu, Chem. Sci., 2018, 9, 1311
DOI: 10.1039/C7SC04827K

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