Visible-Light-Mediated Oxidation of 1-Benzyl-3,4-dihydroisoquinolines with Dioxygen: A Switchable Synthesis of 1-Benzoylisoquinolines and 1-Benzoyl-3,4-dihydroisoquinolines

被引：2

作者：

Ma, Peipei ^{[1
]}

Wu, Hongli ^{[1
]}

Gan, Haifeng ^{[1
]}

机构：

[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, 30 South Puzhu Rd, Nanjing 211816, Jiangsu, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 24期

基金：

中国国家自然科学基金;

关键词：

visible light; 1-benzoylisoquinolines; 1-benzoyl-3,4-dihydroisoquinolines; metal-free; dioxygen; N-HETEROCYCLES; ISOQUINOLINE ALKALOIDS; FREE ACYLATION; C-C; TANDEM; BENZYLISOQUINOLINE; PHOTOCATALYST; OXOAPORPHINE; QUINOLINES; AMIDATION;

D O I：

10.1055/a-2160-8903

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-mediated metal-free oxidation of 1-benzyl-3,4-dihydroisoquinolines (1-BnDHIQs) for the switchable preparation of a wide range of 1-benzoylisoquinolines (BzIQs) and 1-benzoyl-3,4-dihydroisoquinolines (BzDHIQs) is realized using dioxygen as the oxidant. This protocol provides a facile route for the efficient synthesis of isoquinoline alkaloids. Mechanistic investigations suggest that a radical pathway and an ionic pathway may exist simultaneously, with both pathways proceeding via a common key peroxide intermediate to give the oxidized products.

引用

页码：4103 / 4112

页数：10

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