I2-Catalyzed intramolecular dehydrogenative aminooxygenation of alkynes to acylated imidazo[1,2-a]pyridines and indolizines

Yimiao He; Wenqing Yin; Jian Wang; Jianrong Huang; Xinru Pang; Chunfang Gan; Fang Yang; Chusheng Huang

doi:10.1039/C8QO00063H

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I₂-Catalyzed intramolecular dehydrogenative aminooxygenation of alkynes to acylated imidazo[1,2-a]pyridines and indolizines†

Yimiao He,

*^ab Wenqing Yin,

^ab Jian Wang,^c Jianrong Huang,^ab Xinru Pang,^ab Chunfang Gan,^ab Fang Yang^ab and Chusheng Huang*^ab

Author affiliations

* Corresponding authors

^a College of Chemistry and Materials Science, Guangxi Teachers Education University, Nanning 530001, P. R. China
E-mail: heyimiao@gxtc.edu.cn, huangcs@gxtc.edu.cn

^b Guangxi Key Laboratory of Natural Polymer Chemistry and Physics (Guangxi Teachers Education University), Nanning, P. R. China

^c Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, P. R. China

Abstract

An efficient and green protocol for the synthesis of acylated imidazo[1,2-a]pyridines and indolizines via intramolecular dehydrogenative aminooxygenation of alkynes has been developed. The reaction proceeds smoothly utilizing I₂ as a catalyst and TBHP as an oxidant with a broad substrate scope. Mechanism studies reveal that the reaction maybe experiences a hydration followed by an oxidative cycloamination process.

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Article information

DOI: https://doi.org/10.1039/C8QO00063H
Article type: Research Article
Submitted: 19 Jan 2018
Accepted: 26 Mar 2018
First published: 27 Mar 2018

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Org. Chem. Front., 2018,5, 1772-1776

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I₂-Catalyzed intramolecular dehydrogenative aminooxygenation of alkynes to acylated imidazo[1,2-a]pyridines and indolizines

Y. He, W. Yin, J. Wang, J. Huang, X. Pang, C. Gan, F. Yang and C. Huang, Org. Chem. Front., 2018, 5, 1772 DOI: 10.1039/C8QO00063H

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