Issue 9, 2023
From the journal:

Chemical Science

Intramolecular trapping of spiro radicals to produce unusual cyclization products from usual migration substrates†

Jingming Zhang,‡a   Chengkou Liu,‡a   Yaqi Qiao,a   Minghui Wei,a   Wenjing Guan,a   Ziren Mao,a   Hong Qin,a   Zheng Fang ORCID logo *a  and  Kai Guo ORCID logo *ab  

* Corresponding authors

a College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, China
E-mail: fzcpu@njtech.edu.cn, guok@njtech.edu.cn

b State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing, China

Abstract

A conceptually new methodology to give unusual cyclization products from usual migration substrates was disclosed. The highly complex and structurally important and valuable spirocyclic compounds were produced through radical addition, intramolecular cyclization and ring opening instead of usual migration to the di-functionalization products of olefins. Furthermore, a plausible mechanism was proposed based on a series of mechanistic studies including radical trapping, radical clock, verification experiments of intermediates, isotope labeling and KIE experiments.

Graphical abstract: Intramolecular trapping of spiro radicals to produce unusual cyclization products from usual migration substrates

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Article information

DOI
https://doi.org/10.1039/D2SC05768A
Article type
Edge Article
Submitted
18 Oct 2022
Accepted
01 Feb 2023
First published
02 Feb 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 2461-2466

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Intramolecular trapping of spiro radicals to produce unusual cyclization products from usual migration substrates

J. Zhang, C. Liu, Y. Qiao, M. Wei, W. Guan, Z. Mao, H. Qin, Z. Fang and K. Guo, Chem. Sci., 2023, 14, 2461 DOI: 10.1039/D2SC05768A

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