Tuneable access to isoquinolines via a transition-metal-free C(sp3)–C(sp3) bond cleavage rearrangement reaction

Jian Wang; Panyuan Cai; Yimiao He; Yuan Liu; Ling Zhong; Shumin Ding; Yongjia Shang

doi:10.1039/C9QO00427K

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Tuneable access to isoquinolines via a transition-metal-free C(sp³)–C(sp³) bond cleavage rearrangement reaction†

Jian Wang,

‡*^a Panyuan Cai,‡^a Yimiao He,

^b Yuan Liu,^a Ling Zhong,^a Shumin Ding^a and Yongjia Shang

*^a

Author affiliations

* Corresponding authors

^a 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
E-mail: wang_jian989@163.com, shyj@mail.ahnu.edu.cn

^b College of Chemistry and Materials, Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. China

Abstract

A tuneable route to multi-substituted isoquinolines through C–C bond cleavage from ethyl-3-benzyl-3,4-dihydroisoquinoline-3-carboxylate derivatives has been developed. Sodium hydride promoted the formation of 1-(isoquinolin-3-yl)-2-phenylethan-1-ones through a novel rearrangement involving C–C bond cleavage and the formation of a new C–C bond. When ethyl-3-benzyl-3,4-dihydroisoquinoline-3-carboxylates were treated with N-bromosuccinimide, ethyl isoquinoline-3-carboxylates were selectively formed via a radical pathway. These reactions proceed smoothly in moderate to excellent yields under transition-metal-free conditions, and a wide range of functional groups are tolerated.

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Article information

DOI: https://doi.org/10.1039/C9QO00427K
Article type: Research Article
Submitted: 25 Mar 2019
Accepted: 21 May 2019
First published: 24 May 2019

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Org. Chem. Front., 2019,6, 2430-2434

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Tuneable access to isoquinolines via a transition-metal-free C(sp³)–C(sp³) bond cleavage rearrangement reaction

J. Wang, P. Cai, Y. He, Y. Liu, L. Zhong, S. Ding and Y. Shang, Org. Chem. Front., 2019, 6, 2430 DOI: 10.1039/C9QO00427K

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