Issue 24, 2014
From the journal:

Organic & Biomolecular Chemistry

Rhodium(iii)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters. A facile synthesis of functionalized benzolactams†

Hon-Wah Lam,a   Ka-Yi Man,a   Wai-Wing Chan,a   Zhongyuan Zhoua  and  Wing-Yiu Yu*a  

* Corresponding authors

a State Key Laboratory of Chirosciences and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong
E-mail: wing-yiu.yu@polyu.edu.hk
Fax: (+852) 2364-9932

Abstract

A Rh(III)-catalyzed oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters is achieved to afford benzolactams in up to 93% yields. With the N-OAc amido moiety as a directing group, the ortho-C–H is selectively functionalized and the catalytic reaction exhibits excellent tolerance to different functional substituents. A notable rhodacyclic complex is isolated and structurally characterized, suggesting that C–H/N–H cyclometallation is a key step in the catalytic cycle.

Graphical abstract: Rhodium(iii)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters. A facile synthesis of functionalized benzolactams

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C4OB00512K
Article type
Paper
Submitted
07 Mar 2014
Accepted
01 Apr 2014
First published
01 Apr 2014

Org. Biomol. Chem., 2014,12, 4112-4116

Author version available

Download author version (PDF)

Permissions

Request permissions

Rhodium(III)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters. A facile synthesis of functionalized benzolactams

H. Lam, K. Man, W. Chan, Z. Zhou and W. Yu, Org. Biomol. Chem., 2014, 12, 4112 DOI: 10.1039/C4OB00512K

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