Issue 10, 2018

Palladium-catalyzed dimerization of N-aryl propargylamines for the synthesis of 3-vinylquinolines

Abstract

A straightforward method for the synthesis of polyfunctionalized quinolines from readily available N-aryl propargylamines under aerobic conditions was developed. It provides convenient access to a variety of synthetically and pharmaceutically important quinolines in moderate to good yields. Control experiments suggest that the cascade reaction might proceed via the Pd-catalyzed electrophilic cyclization of N-aryl propargylamines followed by a hydroarylation process through trapping of the σ-quinolinylpalladium intermediate with a second molecule of the substrate.

Graphical abstract: Palladium-catalyzed dimerization of N-aryl propargylamines for the synthesis of 3-vinylquinolines

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2018
Accepted
05 Feb 2018
First published
05 Feb 2018

Org. Biomol. Chem., 2018,16, 1736-1744

Palladium-catalyzed dimerization of N-aryl propargylamines for the synthesis of 3-vinylquinolines

X. Li, X. Zhang, B. Hu and X. Zhang, Org. Biomol. Chem., 2018, 16, 1736 DOI: 10.1039/C8OB00133B

To request permission to reproduce material from this article, 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 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