Issue 1, 2015

Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst

Abstract

Pt-loaded HBEA (H+-exchanged BEA zeolite) is found to be an effective and reusable heterogeneous catalyst for regioselective N-alkylation of indoles with primary aliphatic and benzylic alcohols under additive-free conditions driven by the borrowing-hydrogen methodology. Structural and mechanistic studies suggest a cooperative mechanism of the Pt0 site on Pt metal clusters and the Brønsted acid site of the zeolite, in which the Pt0 site is responsible for dehydrogenation/hydrogenation steps and the Brønsted acid site is responsible for the regioselective condensation of indoles with aldehydes to the enamine intermediate.

Graphical abstract: Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst

Supplementary files

Article information

Article type
Communication
Submitted
25 Jul 2014
Accepted
09 Sep 2014
First published
09 Sep 2014

Green Chem., 2015,17, 173-177

Selective N-alkylation of indoles with primary alcohols using a Pt/HBEA catalyst

S. M. A. H. Siddiki, K. Kon and K. Shimizu, Green Chem., 2015, 17, 173 DOI: 10.1039/C4GC01419G

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