Issue 7, 2016

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

Abstract

Direct synthesis of 2,5-disubstituted pyrroles has been achieved via acceptorless dehydrogenative heterocyclization of 1,2-aminoalcohols and secondary alcohols by utilizing a heterogeneous carbon-supported Pt catalyst (Pt/C). The optimized method gave 92% yield of 2-ethyl-5-phenyl-1H-pyrrole as a desired product from 2-amino-1-butanol and 1-phenylethanol in the presence of 0.1 mol% of Pt/C and 1.1 equiv. of KOtBu. It has been revealed that Pt/C demonstrates superior catalytic activity to a number of catalysts tested in this study including other transition metal-loaded carbon and various metal-oxide-supported Pt catalysts. In addition, the turnover number (TON) obtained in the present system was found to be higher than those obtained in previously-reported catalytic systems. It is significant that the Pt/C catalyst could be recycled as a heterogeneous catalyst without significant loss in the activity and showed a wide substrate scope for the 2,5-disubstituted pyrrole forming process.

Graphical abstract: Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

Supplementary files

Article information

Article type
Research Article
Submitted
19 Apr 2016
Accepted
10 Mai 2016
First published
11 Mai 2016

Org. Chem. Front., 2016,3, 846-851

Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts

S. M. A. H. Siddiki, A. S. Touchy, C. Chaudhari, K. Kon, T. Toyao and K. Shimizu, Org. Chem. Front., 2016, 3, 846 DOI: 10.1039/C6QO00165C

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