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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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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 |
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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: | 2 |
Deposited By: | College Office - CoSE |
Deposited On: | 2022-05-16 |
Last Modified: | 2022-05-18 |
Downloads: | 0 |
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