Cyanation and cyanomethylation of trimethylammonium salts via electrochemical cleavage of C-N bonds

被引：36

作者：

Kong, Xianqiang ^{[1
,2
]}

Wang, Yuchang ^{[1
]}

Chen, Yiyi ^{[1
]}

Chen, Xiaohui ^{[1
]}

Lin, Long ^{[2
]}

Cao, Zhong-Yan ^{[3
]}

机构：

[1] Changzhou Inst Technol, Sch Chem Engn & Mat, Changzhou 213032, Peoples R China

[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China

[3] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 05期

基金：

中国国家自然科学基金;

关键词：

PALLADIUM-CATALYZED CYANATION; SANDMEYER CYANATION; PRIMARY AMINES; ARYL; NITRILES; CYANIDE; ALDEHYDES; ACCESS; METAL; CONVERSION;

D O I：

10.1039/d1qo01858b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a practical and mild electrochemical protocol for cyanation and cyanomethylation of trimethylammonium salts through a pathway involving C-N bond cleavage without the need for an external stoichiometric reducing agent or a sacrificial anode. The reaction employs tosyl cyanide (TsCN) or azido allyl alcohol as the cyanation or cyanomethylation reagent, respectively. It shows high functional group compatibility and can be applied for the cyanation of natural product derivatives. Preliminary mechanistic studies indicate the involvement of a radical addition pathway.

引用

页码：1288 / 1294

页数：7

共 60 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] Copper-free Sandmeyer cyanation of arenediazonium o-benzenedisulfonimides [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) :1437-1441

[3] Catalytic Sandmeyer cyanation as a synthetic pathway to aryl nitriles [J].

Beletskaya, IP ;

Sigeev, AS ;

Peregudov, AS ;

Petrovskii, PV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (23) :3810-3812

[4] Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3•OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates [J].

Cao, Liang ;

Luo, Shi-He ;

Jiang, Kai ;

Hao, Zhi-Feng ;

Wang, Bo-Wen ;

Pang, Chu-Ming ;

Wang, Zhao-Yang .

ORGANIC LETTERS, 2018, 20 (16) :4754-4758

[5] Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides [J].

Chmiel, Alyah F. ;

Williams, Oliver P. ;

Chernowsky, Colleen P. ;

Yeung, Charles S. ;

Wickens, Zachary K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (29) :10882-10889

[6] DIRECT ONE-STEP CONVERSION OF ALCOHOLS INTO NITRILES [J].

DAVIS, R ;

UNTCH, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) :2985-2987

[7] Radical cyanomethylation via vinyl azide cascade-fragmentation [J].

Donald, James R. ;

Berrell, Sophie L. .

CHEMICAL SCIENCE, 2019, 10 (22) :5832-5836

[8] Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality [J].

Dutta, Indranil ;

Yadav, Sudhir ;

Sarbajna, Abir ;

De, Subhabrata ;

Hoelscher, Markus ;

Leitner, Walter ;

Bera, Jitendra K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (28) :8662-8666

[9] Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO [J].

Fang, Wan-Yin ;

Qin, Hua-Li .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (09) :5803-5812

[10]

Fatiadi A.J., 1983, Preparation and Synthetic Applications of Cyano Compounds

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