Visible-Light Photoredox Catalyzed Double C-H Functionalization: Radical Cascade Cyclization of Ethers with Benzimidazole-Based Cyanamides

被引：36

作者：

Jiang, Si ^{[1
]}

Tian, Xiao-Jing ^{[1
]}

Feng, Shu-Yao ^{[1
]}

Li, Jiang-Sheng ^{[1
]}

Li, Zhi-Wei ^{[1
]}

Lu, Cui-Hong ^{[1
]}

Li, Chao-Jun ^{[2
,3
]}

Liu, Wei-Dong ^{[4
]}

机构：

[1] Changsha Univ Sci & Technol, Sch Chem & Food Engn, Hunan Prov Key Lab Mat Protect Elect Power & Tran, Changsha 410114, Peoples R China

[2] McGill Univ, Dept Chem, Sherbrooke, PQ H3A 0B8, Canada

[3] McGill Univ, FQRNT Ctr Green Chem & Catalysis, Sherbrooke, PQ H3A 0B8, Canada

[4] Hunan Res Inst Chem Ind, Natl Engn Res Ctr Agrochem, Changsha 410007, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 03期

基金：

国家重点研发计划;

关键词：

QUINAZOLINONES;

D O I：

10.1021/acs.orglett.0c03853

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light photoredox catalyzed radical cascade cyclization of simple ethers with cyanamides is developed at room temperature. This strategy involves sequential inert C-sp3-H/C-sp2-H functionalizations through intermolecular addition reaction of oxyalkyl radicals to N-cyano groups followed by radical cyclization of iminyl radicals in situ generated with C-2 aryl rings. This method allows for efficient synthesis of tetracyclic benzo[4,5]imidazo[1,2-c]quinazolines. Importantly, this is the first example of an intermolecular-intramolecular radical cascade cyclization reaction of cyanamides.

引用

页码：692 / 696

页数：5

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