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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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Title: Synthesis of 2,5-disubstituted pyrroles via dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols by supported platinum catalysts
Authors: Siddiki, S. M. A. H. Browse this author
Touchy, Abeda S. Browse this author
Chaudhari, Chandan Browse this author
Kon, Kenichi Browse this author
Toyao, Takashi Browse this author →KAKEN DB
Shimizu, Ken-ichi Browse this author →KAKEN DB
Issue Date: 1-Jul-2016
Publisher: RSC Publishing
Journal Title: Organic chemistry frontiers
Volume: 3
Issue: 7
Start Page: 846
End Page: 851
Publisher DOI: 10.1039/c6qo00165c
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.
Rights: © the Partner Organisations 2016
Type: article (author version)
URI: http://hdl.handle.net/2115/66435
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 清水 研一

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