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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]


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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 CH bond functionalisation of organic molecules provide one of the cornerstones of modern chemical synthesis. In chloroalkane synthesis, such methods for intermolecular site-selective aliphatic CH 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 CH bond functionalisation. By unlocking dichloramine-Ts 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

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