eCite Digital Repository
Copper(I)-catalysed site-selective C(sp3)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T
Citation
Jin, J and Zhao, Y and Kyne, SH and Farshadfar, K and Ariafard, A and Chan, PWH, Copper(I)-catalysed site-selective C(sp3)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T, Nature Communications, 12, (1) Article 4065. ISSN 2041-1723 (2021) [Refereed Article]
![]() | PDF (Published version) 1Mb |
Copyright Statement
Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons 4.0 International (CC BY 4.0) license (https://creativecommons.org/licenses/by/4.0/).
DOI: doi:10.1038/s41467-021-23988-y
Abstract
Strategies that enable intermolecular site-selective C–H bond functionalisation of organic molecules provide one of the cornerstones of modern chemical synthesis. In chloroalkane synthesis, such methods for intermolecular site-selective aliphatic C–H bond chlorination have, however, remained conspicuously rare. Here, we present a copper(I)-catalysed synthetic method for the efficient site-selective C(sp3)–H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T at room temperature. A key feature of the broad substrate scope is tolerance to unsaturation, which would normally pose an immense challenge in chemoselective aliphatic C–H bond functionalisation. By unlocking dichloramine-T’s potential as a chlorine radical atom source, the product site-selectivities achieved are among the most selective in alkane functionalisation and should find widespread utility in chemical synthesis. This is exemplified by the late-stage site-selective modification of a number of natural products and bioactive compounds, and gram-scale preparation and formal synthesis of two drug molecules.
Item Details
Item Type: | Refereed Article |
---|---|
Keywords: | copper catalysis, reaction mechanism, DFT calculations, C-H activation |
Research Division: | Chemical Sciences |
Research Group: | Physical chemistry |
Research Field: | Catalysis and mechanisms of reactions |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
ID Code: | 150054 |
Year Published: | 2021 |
Web of Science® Times Cited: | 3 |
Deposited By: | College Office - CoSE |
Deposited On: | 2022-05-16 |
Last Modified: | 2022-08-18 |
Downloads: | 12 View Download Statistics |
Repository Staff Only: item control page