Ni-Mediated Generation of "CN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

被引：56

作者：

Yang, Luo ^{[1
]}

Liu, Yu-Ting ^{[1
]}

Park, Yoonsu ^{[2
,3
]}

Park, Sung-Woo ^{[2
,3
]}

Chang, Sukbok ^{[2
,3
]}

机构：

[1] Xiangtan Univ, Coll Chem, Key Lab Green Organ Synth & Applicat Hunan Prov, Xiangtan 411105, Hunan, Peoples R China

[2] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea

[3] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 34141, South Korea

来源：

ACS CATALYSIS | 2019年 / 9卷 / 04期

基金：

中国国家自然科学基金;

关键词：

cyano source; formamide; Ni catalyst; hydrocyanation; alkynes; aryl halides; ELECTROPHILIC CYANATION; AMMONIUM IODIDE; ARYL; NITRILES; BOND; CHEMISTRY; EFFICIENT; INDOLES; CYANIDE; HYDROCYANATION;

D O I：

10.1021/acscatal.8b05111

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

引用

页码：3360 / 3365

页数：11

共 65 条

[1] Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles [J].

Anbarasan, Pazhamalai ;

Schareina, Thomas ;

Beller, Matthias .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5049-5067

[2] A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids [J].

Anbarasan, Pazhamalai ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :519-522

[3] A Convenient Synthesis of Benzonitriles via Electrophilic Cyanation with N-Cyanobenzimidazole [J].

Anbarasan, Pazhamalai ;

Neumann, Helfried ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) :4725-4728

[4]

[Anonymous], 1999, COMPREHENSIVE ORGANI

[5] Hydrocyanative Cyclization and Three-Component Cross-Coupling Reaction between Allenes and Alkynes under Nickel Catalysis [J].

Arai, Shigeru ;

Amako, Yuka ;

Yang, Xiaofei ;

Nishida, Atsushi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :8147-8150

[6]

Babler P., 2006, U.S. Patent, Patent No. [2006/0110309, 20060110309]

[7]

Bhattacharyya N.K., 2012, International Journal of Chemistry and Applications, V4, P295

[8] AlCl3•6H2O/KI/H2O/CH3CN:: A new alternate system for dehydration of oximes and amides in hydrated media [J].

Boruah, M ;

Konwar, D .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7138-7139

[9] Rhodium-Catalyzed Cyanation of C(sp2)-H Bond of Alkenes [J].

Chaitanya, Manthena ;

Anbarasan, Pazhamalai .

ORGANIC LETTERS, 2015, 17 (15) :3766-3769

[10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

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