Issue 5, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2018,9, 1311-1316

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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