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Issue 7, 2016

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

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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


Submitted
19 Apr 2016
Accepted
10 May 2016
First published
11 May 2016

Org. Chem. Front., 2016,3, 846-851
Article type
Research Article

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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