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


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.

SUBMITTER: Jin J 

PROVIDER: S-EPMC8249392 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Copper(I)-catalysed site-selective C(sp<sup>3</sup>)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T.

Jin Jianwen J   Zhao Yichao Y   Kyne Sara Helen SH   Farshadfar Kaveh K   Ariafard Alireza A   Chan Philip Wai Hong PWH  

Nature communications 20210701 1


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(sp<sup>3</sup>)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T a  ...[more]

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