Radical heteroarylation of unactivated remote C(sp3)–H bonds via intramolecular heteroaryl migration

Zhu Cao; Huihui Zhang; Xinxin Wu; Yahong Li; Chen Zhu

doi:10.1039/D1QO01209F

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Radical heteroarylation of unactivated remote C(sp³)–H bonds via intramolecular heteroaryl migration†

Zhu Cao,‡^a Huihui Zhang,‡^a Xinxin Wu,^a Yahong Li

*^a and Chen Zhu

*^ab

Author affiliations

* Corresponding authors

^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China
E-mail: chzhu@suda.edu.cn, liyahong@suda.edu.cn

^b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China

Abstract

The radical-mediated heteroarylation of unactivated remote C(sp³)–H bonds via intramolecular heteroaryl migration is achieved, leading to a variety of heteroaryl-substituted aliphatic ketones. A library of O-/S-/N-containing heteroaryls such as benzofuryl, benzothiazolyl, benzothienyl, benzoxazolyl, oxazolyl, and thiazolyl are amenable to the migration approach. The heteroaryl migration is triggered by an azido radical-mediated hydrogen atom abstraction from unactivated aliphatic C(sp³)–H bonds. The transformation features mild C–C bond cleavage, good selectivity for tertiary C(sp³)–H bonds, and broad functional group compatibility.

This article is part of the themed collection: FOCUS: Radical-involved chemical transformations

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Article information

DOI: https://doi.org/10.1039/D1QO01209F
Article type: Research Article
Submitted: 12 Aug 2021
Accepted: 18 Sep 2021
First published: 20 Sep 2021

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Org. Chem. Front., 2021,8, 6395-6399

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Radical heteroarylation of unactivated remote C(sp³)–H bonds via intramolecular heteroaryl migration

Z. Cao, H. Zhang, X. Wu, Y. Li and C. Zhu, Org. Chem. Front., 2021, 8, 6395 DOI: 10.1039/D1QO01209F

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