Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles

Zhe Chang, Jialin Huang, Si Wang, Geshuyi Chen, Heng Zhao, Rui Wang () and Depeng Zhao ()
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Zhe Chang: Sun Yat-Sen University
Jialin Huang: Sun Yat-Sen University
Si Wang: Sun Yat-Sen University
Geshuyi Chen: Lanzhou University
Heng Zhao: Sun Yat-Sen University
Rui Wang: Lanzhou University
Depeng Zhao: Sun Yat-Sen University

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Nitrogen heterocycle represents a ubiquitous skeleton in natural products and drugs. Late-stage C(sp3)-H bond functionalization of N-heterocycles with broad substrate scope remains a challenge and of particular significance to modern chemical synthesis and pharmaceutical chemistry. Here, we demonstrate copper-catalysed late-stage C(sp3)-H functionalizaion of N-heterocycles using commercially available catalysts under mild reaction conditions. We have investigated 8 types of N-heterocycles which are usually found as medicinally important skeletons. The scope and utility of this approach are demonstrated by late-stage C(sp3)-H modification of these heterocycles including a number of pharmaceuticals with a broad range of nucleophiles, e.g. methylation, arylation, azidination, mono-deuteration and glycoconjugation etc. Preliminary mechanistic studies reveal that the reaction undergoes a C-H fluorination process which is followed by a nucleophilic substitution.

Date: 2021
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DOI: 10.1038/s41467-021-24671-y

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