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

收藏

页码：4965 / 4969

页数：5

相关论文

共 50 条

[31] Nickel-Catalyzed Three-Component Cycloadditions of Enoates, Alkynes, and Aldehydes [J].

Jenkins, Aireal D. ;

Robo, Michael T. ;

Zimmerman, Paul M. ;

Montgomery, John .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (05) :2956-2965

[32] Nickel-Catalyzed Synthesis of Diarylamines via Oxidatively Induced C-N Bond Formation at Room Temperature [J].

Illies, Laurean ;

Matsubara, Tatsuaki ;

Nakamura, Eiichi .

ORGANIC LETTERS, 2012, 14 (21) :5570-5573

[33] Regioselective Synthesis of Trialkylpyrazines via Nickel-Catalyzed Negishi Cross-Coupling of Pyrazine Triflate [J].

Pitchaiah, Arigala ;

Hwang, In Taek ;

Hwang, Jin-Soo ;

Kim, Hyungrok ;

Lee, Kee-In .

SYNTHESIS-STUTTGART, 2012, 44 (11) :1631-1636

[34] Nickel-Catalyzed Synthesis of Quinazolinediones [J].

Beutner, Gregory L. ;

Hsiao, Yi ;

Razler, Thomas ;

Simmons, Eric M. ;

Wertjes, William .

ORGANIC LETTERS, 2017, 19 (05) :1052-1055

[35] Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination [J].

Dhungana, Roshan K. ;

Aryal, Vivek ;

Niroula, Doleshwar ;

Sapkota, Rishi R. ;

Lakomy, Margaret G. ;

Giri, Ramesh .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (35) :19092-19096

[36] Synthesis of Multisubstituted Allenes via Nickel-Catalyzed Cross-Electrophile Coupling [J].

Jin, Youxiang ;

Wen, Hao ;

Yang, Feiyan ;

Ding, Decai ;

Wang, Chuan .

ACS CATALYSIS, 2021, 11 (21) :13355-13362

[37] Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition [J].

Jenkins, Aireal D. ;

Herath, Ananda ;

Song, Minsoo ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) :14460-14466

[38] Synthesis of Quinolones by Nickel-Catalyzed Cycloaddition via Elimination of Nitrile [J].

Nakai, Kenichiro ;

Kurahashi, Takuya ;

Matsubara, Seijiro .

ORGANIC LETTERS, 2013, 15 (04) :856-859

[39] New nickel-catalyzed carbozincation of alkynes: A short synthesis of (Z)-tamoxifen [J].

Studemann, T ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :93-95

[40] Nickel-Catalyzed Cycloadditions of Thiophthalic Anhydrides with Alkynes [J].

Inami, Tasuku ;

Baba, Yoko ;

Kurahashi, Takuya ;

Matsubara, Seijiro .

ORGANIC LETTERS, 2011, 13 (08) :1912-1915

← 1 2 3 4 5 →