Issue 22, 2021

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
12 Aug. 2021
Accepted
18 Sept. 2021
First published
20 Sept. 2021

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

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements