Redox-Neutral Generation of Iminyl Radicals by N-Heterocyclic Carbene Catalysis: Rapid Access to Phenanthridines from Vinyl Azides

被引：31

作者：

Liu, Lixia ^{[1
]}

Zhang, Qijing ^{[1
]}

Wang, Chengming ^{[1
]}

机构：

[1] Jinan Univ, Coll Chem & Mat Sci, Guangdong Prov Key Lab Funct Supramol Coordinat M, Guangzhou 511443, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 32期

关键词：

CYCLIZATION;

D O I：

10.1021/acs.orglett.2c02118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-heterocyclic carbene-catalyzed oxidant-, metal-and light-free iminyl radical generation pathway stemming from the reaction of vinyl azide and alpha-bromo ester is uncovered. This newly developed methodology is successfully applied to the redox-neutral construction of a number of diversified phenan-thridine derivatives with nice functional group compatibility. Insights from the mechanism study reveal that this NHC-catalyzed transformation potentially proceeds through an alkyl radical addition-initiated HAS process, with the iminyl radical as an active intermediate <comment>Superscript/Subscript Available</comment

引用

页码：5913 / 5917

页数：5

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