C-H Cyanoalkylation:the direct C-H Cyanomethylation of Naphthalimide

被引:0
作者
Chen, Xi [1 ]
Li, Zheyao [1 ]
Chen, Yayun [1 ]
Chen, Zhihua [1 ]
Hu, Yan [1 ]
Liu, Chuanxiang [1 ]
机构
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 201418, Peoples R China
基金
上海市自然科学基金;
关键词
cyanomethylation; C-H functionalization; radical; directing group; naphthalimide; ALPHA-ARYL NITRILES; ACTIVATED ALKENES; C(SP(3))-H BONDS; ALKYL NITRILES; ARYLATION; ALCOHOLS; ACIDS;
D O I
10.7536/PC201001
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The cyanoalkylation/ cyanomethylation of organic molecules is of great research interest to organic and medicinal chemists due to the wide presence of the cyano group in biologically active molecules and the facile conversion of the cyano group into many other functional groups, such as amides, esters, aldehydes, and primary amines. Although a variety of different synthetic strategies have been developed for the selective introduction of the cyanomethyl group, an attractive approach is to use acetonitrile directly through C-H activation due to the highly efficient atom economy and the avoidance of prefunctionalization. Therefore, this review summarizes the main research progress in C-H cyanoalkylation/ cyanomethylation of radical cyanomethylation, Photochemical Cross over line coupling reaction, Cross over line Dehydrogenative Coupling ( CDC) Reaction, Directing group over line promoted C-H cyanomethylation and Fluorophore C-H cyanomethylation reported by our group.
引用
收藏
页码:1947 / 1952
页数:6
相关论文
共 41 条
[1]  
Bacchi S., 2010, SYNTHESIS, V2010, P3332
[2]   Synthesis of Functionalized Epoxides by Copper-Catalyzed Alkylative Epoxidation of Allylic Alcohols with Alkyl Nitriles [J].
Bunescu, Ala ;
Wang, Qian ;
Zhu, Jieping .
ORGANIC LETTERS, 2015, 17 (08) :1890-1893
[3]   Copper-Catalyzed Intermolecular Carboetherification of Unactivated Alkenes by Alkyl Nitriles and Alcohols [J].
Chatalova-Sazepin, Claire ;
Wang, Qian ;
Sammis, Glenn M. ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (18) :5443-5446
[4]   Facile Preparation of α-Aryl Nitriles by Direct Cyanation of Alcohols with TMSCN Under the Catalysis of InX3 [J].
Chen, Gang ;
Wang, Zheng ;
Wu, Jiang ;
Ding, Kuiling .
ORGANIC LETTERS, 2008, 10 (20) :4573-4576
[5]   A novel chemodosimeter for fluoride ions based on deprotonation of the C-H group followed by an autoxidative decyanation process [J].
Chen, Jinju ;
Liu, Chuanxiang ;
Zhang, Jiali ;
Ding, Wen ;
Zhou, Min ;
Wu, Fanhong .
CHEMICAL COMMUNICATIONS, 2013, 49 (92) :10814-10816
[6]   A reusable cyanide sensor via activation of C-H group: trifluoromethylcarbinol-directed meta-C-H cyanomethylation of naphthalimide [J].
Chen, Yayun ;
Hu, Xiaoxue ;
Rao, Caihui ;
Li, Zheyao ;
Chen, Lu ;
Fu, Chao ;
Liu, Chuanxiang .
ANALYST, 2018, 143 (19) :4655-4661
[7]   Carboxylic Acids as Traceless Directing Groups for Formal meta-Selective Direct Arylation [J].
Cornella, Josep ;
Righi, Marika ;
Larrosa, Igor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) :9429-9432
[8]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[9]   CONDENSATION OF AROMATIC NITRO COMPOUNDS WITH ACRYLACETONITRILES .2. SOME PARA-SUBSTITUTED NITROBENZENES [J].
DAVIS, RB ;
PIZZINI, LC .
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (11) :1884-1888
[10]   Addition of Metal Enolate Derivatives to Unactivated Carbon-Carbon Multiple Bonds [J].
Denes, Fabrice ;
Perez-Luna, Alejandro ;
Chemla, Fabrice .
CHEMICAL REVIEWS, 2010, 110 (04) :2366-2447