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]


Preview
PDF
Pending copyright assessment - Request a copy
1Mb
  

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

Repository Staff Only: item control page