Electrooxidative iridium-catalyzed sp2 C-H activation-annulation leading to cationic π-extended heteroaromatics

被引：3

作者：

Yang, Qi-Liang ^{[1
]}

Guo, Na-Na ^{[1
]}

Liu, Shu-Xian ^{[1
]}

Zhang, Bei-Ning ^{[1
]}

Zou, Guodong ^{[2
]}

Wang, Hai-Xia ^{[1
]}

Wang, Dong-Chao ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine C, Sch Chem & Chem Engn,State Key Lab Antiviral Drugs, Key Lab Green Chem Media & React,Pingyuan Lab,Mini, Xinxiang 453007, Henan, Peoples R China

[2] Xinyang Normal Univ, Coll Chem & Chem Engn, Xinyang 464000, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 17期

基金：

中国国家自然科学基金;

关键词：

BOND ACTIVATION; MERGING ELECTROCHEMISTRY; ISOQUINOLINIUM SALTS; ALKYNES; ACCESS; RHODIUM; METALLAELECTROCATALYSIS; OXYGENATION; C(SP(3))-H; ROUTE;

D O I：

10.1039/d4qo01019a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This study demonstrates an electrochemically driven, Ir(III)-catalyzed method for pyridine-, azo-, and purine-directed olefinic and aromatic C(sp(2))-H activation and regioselective annulation with alkynes for the synthesis of biologically useful quaternary ammonium salts. This approach notably eliminates the need for stoichiometric amounts of external oxidants, offering a broader substrate scope along with improved product regioselectivity under mild electrolysis conditions as compared to previously employed strong oxidant conditions. Detailed mechanistic insights, including the isolation, characterization, and cyclovoltammetric analysis of catalytically relevant iridium(iii) and iridium(i) intermediates, provided strong supporting evidence for an Ir(III/I) catalytic cycle operation.

引用

页码：4849 / 4856

页数：8

共 74 条

[1] UNUSUALLY MILD AND SELECTIVE HYDROCARBON C-H BOND ACTIVATION WITH POSITIVELY CHARGED IRIDIUM(III) COMPLEXES [J].