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
收藏
页码：4103 / 4112
页数：10
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