Visible light mediated sp3 C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type three-component reaction

被引：52

作者：

Chen, Yunyun ^{[1
]}

Feng, Gaofeng ^{[1
]}

机构：

[1] Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 14期

基金：

中国国家自然科学基金;

关键词：

DEHYDROGENATIVE-COUPLING REACTION; CATALYZED OXIDATIVE CYANATION; TERTIARY-AMINES; MOLECULAR-OXYGEN; MULTICOMPONENT REACTIONS; ISOQUINOLINE ALKALOIDS; HYDROGEN-PEROXIDE; ORGANIC-SYNTHESIS; SODIUM-CYANIDE; NITROGEN ATOM;

D O I：

10.1039/c5ob00201j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and high yield process for sp(3) C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines is disclosed. This involves a visible light mediated photoredox Ugi-type reaction with carboxylic acids and isonitriles under aerobic conditions, employing Ru(bpy)(3)Cl-2 as a photoredox catalyst and CH3CN as the solvent. CH3CN was found to be crucial for the process, and good to excellent yields were achieved for a wide variety of N-aryl-1,2,3,4-tetrahydroisoquinolines, carboxylic acids, and isonitriles. The developed methodology is attractive for the synthesis of a library of 1,2,3,4-tetrahydroisoquinolines.

引用

页码：4260 / 4265

页数：6

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