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 11月 2017
Accepted
08 12月 2017
First published
08 12月 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements