Jump to main content
Jump to site search

Issue 42, 2014
Previous Article Next Article

The mechanism and regioselectivity of gold(i) or platinum(ii) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones

Author affiliations

Abstract

We report here the theoretical analysis of the mechanism and regioselectivity of gold(I) or platinum(II) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones. AuPH3+ and PtCl2 have been considered to account for some experimental observations. Our calculation results indicate that in the case of cationic gold the nucleophilic attack of the pyrrole on the activated alkyne occurs in an exo-dig fashion generating a six-membered intermediate, which upon deprotonation and protodeauration forms pyrrolopyridinone. When platinum is used, an endo-dig fashion is observed generating a seven-membered intermediate. After deprotonation and protodeplatination pyrroloazepinone is formed. Whether for exo-dig (gold(I)) or endo-dig (platinum(II)) cyclization, a [1,2]-migration would not be needed.

Graphical abstract: The mechanism and regioselectivity of gold(i) or platinum(ii) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones

Back to tab navigation

Supplementary files

Article information


Submitted
01 May 2014
Accepted
29 Aug 2014
First published
01 Sep 2014

Org. Biomol. Chem., 2014,12, 8433-8441
Article type
Paper
Author version available

The mechanism and regioselectivity of gold(I) or platinum(II) catalyzed intramolecular hydroarylation to pyrrolopyridinones and pyrroloazepinones

R. Fang, X. Wei and L. Yang, Org. Biomol. Chem., 2014, 12, 8433 DOI: 10.1039/C4OB00894D

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

Search articles by author

Spotlight

Advertisements