Mechanistic studies on the atmosphere and light tuned synthesis of cyclobuta/penta[b]indoles

被引：11

作者：

Cao, Bo ^{[1
,2
]}

Wei, Yin ^{[3
]}

Ye, Chen ^{[4
]}

Wu, Li-Zhu ^{[4
]}

Shi, Min ^{[1
,2
,3
,5
,6
]}

机构：

[1] East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

[2] East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Ctr Excellence Mol Synth,Univ Chinese Acad Sci, 345 Lingling Rd, Shanghai 200032, Peoples R China

[4] Chinese Acad Sci, Key Lab Photochem Convers & Optoelect Mat, Tech Inst Phys & Chem, Univ Chinese Acad Sci, Shanghai, Peoples R China

[5] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[6] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 12期

基金：

中国国家自然科学基金;

关键词：

TRANSITION-METAL-FREE; ARYL DIAZONIUM SALTS; VISIBLE-LIGHT; PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; MOLECULAR-OXYGEN; CASCADE REACTION; RADICAL CATIONS; GREEN CHEMISTRY; ALKYNES;

D O I：

10.1039/c8qo00306h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta [b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes has been investigated using kinetic and spectroscopic methods. The mechanistic studies indicate that the reaction undergoes hydroamination through aza-Michael addition, [2 + 2] cycloaddition to furnish the cyclobuta[b] indoles, and a photocatalytic process assisted by molecular oxygen to form the cyclopenta[b] indoles. Oxygen acts as a redox catalyst under household light irradiation in this process. An important triplet intermediate has been observed using time-resolved transient absorption spectroscopy.

引用

页码：1890 / 1895

页数：6

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