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Nat Commun ; 12(1): 4065, 2021 07 01.
Artigo em Inglês | MEDLINE | ID: mdl-34210971

RESUMO

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.


Assuntos
Domínio Catalítico , Cobre/química , Cetonas/química , Sulfonamidas/química , Produtos Biológicos/química , Carbono/química , Catálise , Halogenação , Hidrogênio/química , Temperatura
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