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氰基-2,2'-联苯二羰二亚胺作为氰化试剂在离子液体中钴(III)催化吲哚 C-H 氰化反应。

-Cyano-2,2'-biphenyldicarboimide as a Cyanation Reagent for Co(III)-Catalyzed C-H Cyanation of Indoles in Ionic Liquids.

机构信息

School of Chemistry and Materials Science, Heilongjiang University, Harbin, Heilongjiang 150080, P.R. China.

出版信息

Org Lett. 2023 Mar 10;25(9):1436-1440. doi: 10.1021/acs.orglett.3c00164. Epub 2023 Mar 1.

Abstract

A mild strategy for Co(III)-catalyzed C(sp)-H cyanation of indoles was developed by using NCBLD as an electrophilic cyanation reagent and 1-butyl-3-acetylimidazole ditrifluoromethylsulfonimide ([BAIM]NTf) as an environmentally friendly and recyclable solvent, and a series of 2-cyano products were obtained at room temperature. Adopting this strategy, the unnatural nucleotide fragment precursor of Remdesivir, which was a drug for COVID-19, was synthesized through cyano transformation, further proving the practicability of this cyanation method.

摘要

开发了一种温和的策略,通过使用 NCBLD 作为亲电氰化试剂和 1-丁基-3-乙酰咪唑二三氟甲磺酰亚胺 ([BAIM]NTf) 作为环保且可回收的溶剂,实现了 Co(III)催化吲哚的 C(sp)-H 氰化反应,在室温下得到了一系列 2-氰基产物。采用该策略,通过氰基转化合成了瑞德西韦(一种 COVID-19 药物)的非天然核苷酸片段前体,进一步证明了该氰化方法的实用性。

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