Issue 71, 2021

Tropylium-promoted Ritter reactions

Abstract

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuable N-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

Graphical abstract: Tropylium-promoted Ritter reactions

Supplementary files

Article information

Article type
Communication
Submitted
04 Jūn. 2021
Accepted
09 Aug. 2021
First published
09 Aug. 2021

Chem. Commun., 2021,57, 8901-8904

Tropylium-promoted Ritter reactions

S. H. Doan, M. A. Hussein and T. V. Nguyen, Chem. Commun., 2021, 57, 8901 DOI: 10.1039/D1CC02947A

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