Issue 28, 2019

Practical, metal-free remote heteroarylation of amides via unactivated C(sp3)–H bond functionalization

Abstract

Development of practical methods for the production of multi-functionalized amides is one of the most important topics in both synthetic chemistry and drug discovery. Disclosed herein is a new, efficient, site-selective heteroarylation of amides via C(sp3)–H bond functionalization. Amidyl radicals are directly generated from the amide N–H bonds under mild conditions, which trigger the subsequent 1,5-HAT process. A wide scope of aliphatic amides including carboxamides, sulfonamides, and phosphoramides are readily modified at remote C(sp3)–H bonds by installing diverse heteroaryl groups. Borne out of pragmatic consideration, this protocol can be used for the late-stage functionalization of amides.

Graphical abstract: Practical, metal-free remote heteroarylation of amides via unactivated C(sp3)–H bond functionalization

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Maijs 2019
Accepted
10 Jūn. 2019
First published
11 Jūn. 2019
This article is Open Access

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

Chem. Sci., 2019,10, 6915-6919

Practical, metal-free remote heteroarylation of amides via unactivated C(sp3)–H bond functionalization

N. Tang, X. Wu and C. Zhu, Chem. Sci., 2019, 10, 6915 DOI: 10.1039/C9SC02564B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements