Copper(I)-catalysed site-selective C(sp3)–H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T

Jianwen Jin, Yichao Zhao, Sara Helen Kyne, Kaveh Farshadfar, Alireza Ariafard () and Philip Wai Hong Chan ()
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Jianwen Jin: Monash University
Yichao Zhao: Monash University
Sara Helen Kyne: Monash University
Kaveh Farshadfar: Islamic Azad University
Alireza Ariafard: Islamic Azad University
Philip Wai Hong Chan: Monash University

Nature Communications, 2021, vol. 12, issue 1, 1-12

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-23988-y

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