Issue 42, 2014

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

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

Supplementary files

Article information

Article type
Paper
Submitted
01 May 2014
Accepted
29 Aug 2014
First published
01 Sep 2014

Org. Biomol. Chem., 2014,12, 8433-8441

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

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