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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
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)
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Submitter: 清水 研一
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