Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature

被引：11

作者：

Sun, Jian-Guo ^{[1
]}

Zhang, Xiao-Yu ^{[1
]}

Yang, Hua ^{[1
]}

Li, Ping ^{[1
]}

Zhang, Bo ^{[1
]}

机构：

[1] China Pharmaceut Univ, State Key Lab Nat Med, 24 Tongjia Xiang, Nanjing 210009, Jiangsu, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 35期

基金：

中国国家自然科学基金;

关键词：

Earth-abundant metals; Alkynes; Isoquinolines; Annulation; Nickel; Regioselectivity; CROSS-COUPLING REACTIONS; C-O; PALLADIUM; ANNULATION; ALKALOIDS; AMINATION; PYRIDINES; ARYL; HETEROCYCLES; CYCLIZATION;

D O I：

10.1002/ejoc.201800341

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl-2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.

引用

页码：4965 / 4969

页数：5

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