NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds

Yuqi Zhang; Xiaojing Ye; Sicheng Liu; Wei Chen; Irfan Majeed; Tingting Liu; Yulin Zhu; Zhuo Zeng

doi:10.1039/D1OB01409A

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds†

Yuqi Zhang,^a Xiaojing Ye,^a Sicheng Liu,^a Wei Chen,^a Irfan Majeed,^a Tingting Liu,*^a Yulin Zhu*^a and Zhuo Zeng

*^ab

Author affiliations

* Corresponding authors

^a College of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
E-mail: zhuoz@scnu.edu.cn

^b Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, China

Abstract

Multifunctional transformation of amide C–N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.

This article is part of the themed collection: Synthetic methodology in OBC

Download options Please wait...

Supplementary files

Supplementary information PDF (2613K)

Article information

DOI: https://doi.org/10.1039/D1OB01409A
Article type: Paper
Submitted: 20 Jul 2021
Accepted: 31 Aug 2021
First published: 01 Sep 2021

Download Citation

Org. Biomol. Chem., 2021,19, 8566-8571

Permissions

Request permissions

NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds

Y. Zhang, X. Ye, S. Liu, W. Chen, I. Majeed, T. Liu, Y. Zhu and Z. Zeng, Org. Biomol. Chem., 2021, 19, 8566 DOI: 10.1039/D1OB01409A

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.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Organic & Biomolecular Chemistry

NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds†

Abstract

Supplementary files

Article information

Download Citation

Permissions

NaOTs-promoted transition metal-free C–N bond cleavage to form C–X (X = N, O, S) bonds

Social activity

Search articles by author

Spotlight

Advertisements