Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp3)–H functionalization

Jie Li; Wen-Juan Hao; Peng Zhou; Yi-Long Zhu; Shu-Liang Wang; Shu-Jiang Tu; Bo Jiang

doi:10.1039/C6RA28589A

Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp³)–H functionalization†

Jie Li,^a Wen-Juan Hao,*^a Peng Zhou,^a Yi-Long Zhu,^ab Shu-Liang Wang,^a Shu-Jiang Tu^a and Bo Jiang

*^a

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China
E-mail: wjhao@jsnu.edu.cn, jiangchem@jsnu.edu.cn
Fax: +86 51683500065
Tel: +86 51683500065

^b Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, Jiangsu, P. R. China

Abstract

A new Ag-catalyzed oxidative bicyclization of N-tethered 1,7-enynes with alkylcarboxylic acids for forming 41 examples of polycyclic 3,4-dihydroquinolin-2(1H)-ones has been established using readily accessible K₂S₂O₈ as an oxidant. The reaction pathway involves a silver-catalyzed decarboxylation/in situ-generated C-center radical-triggered α,β-conjugated addition/6-exo-dig cyclization/H-abstraction/5-endo-trig cyclization/SET sequence, allowing direct site-selective decarboxylative C(sp³)–H functionalization toward the formation of multiple C–C bonds and rapid construction of complex spiroheterocycles.

This article is part of the themed collection: Editors’ collection: Catalytic Organic Transformations

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DOI: https://doi.org/10.1039/C6RA28589A
Article type: Paper
Submitted: 22 Dec 2016
Accepted: 28 Jan 2017
First published: 02 Feb 2017
This article is Open Access

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RSC Adv., 2017,7, 9693-9703

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Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp³)–H functionalization

J. Li, W. Hao, P. Zhou, Y. Zhu, S. Wang, S. Tu and B. Jiang, RSC Adv., 2017, 7, 9693 DOI: 10.1039/C6RA28589A

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