Issue 31, 2012
From the journal:

Organic & Biomolecular Chemistry

Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?†

Zhe Li*a  and  Hai-Xiang Gaoa  

* Corresponding authors

a Department of Applied Chemistry, China Agricultural University, Beijing, China
E-mail: lizhe@cau.edu.cn
Tel: +86-15101058007

Abstract

The mechanism of the title reaction is found to consist of three steps by DFT calculations: (1) N2 dissociation, (2) intramolecular Ag-carbene addition, and (3) proton transfer. The N2 dissociation is turnover determining. The product 3-alkylideneoxindole is favored in tautomerization with 3-acetyl-2-hydroxyindole.

Graphical abstract: Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB25581B
Article type
Paper
Submitted
19 Mar 2012
Accepted
13 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 6294-6298

Permissions

Request permissions

Theoretical study on the mechanism of Ag-catalyzed synthesis of 3-alkylideneoxindoles from N-aryl-α-diazoamides: a Lewis acid or Ag-carbene pathway?

Z. Li and H. Gao, Org. Biomol. Chem., 2012, 10, 6294 DOI: 10.1039/C2OB25581B

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