N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes

被引：111
作者：
Liu, Songbai [1 ]
Yu, Ying [1 ]
Liebeskind, Lanny S. [1 ]
机构：
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 10期
关键词：
D O I：
10.1021/ol070561w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalytic quantities of copper(I) or copper(II) sources catalyze the N-imination of boronic acids and organostannanes through reaction with oxime O-carboxylates under nonbasic conditions. This method tolerates various functional groups and takes place efficiently using aryl, heteroaryl, and alkenyl boronic acids and stannanes.
引用
收藏
页码：1947 / 1950
页数：4
相关论文
共 50 条
[21]   Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines [J].
Smith, Joshua J. ;
Best, Daniel ;
Lam, Hon Wai .
CHEMICAL COMMUNICATIONS, 2016, 52 (19) :3770-3772
[22]   Synthesis of N-1-aryl-purine nucleosides using copper-catalyzed C-N coupling of boronic acids [J].
Strouse, JJR ;
Jeselnik, M ;
Arterburn, JB .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 :U187-U187
[23]   Base and ligand free copper-catalyzed N-arylation of 2-amino-N-heterocycles with boronic acids in air [J].
Rao, D. Nageswar ;
Rasheed, Sk. ;
Aravinda, S. ;
Vishwakarma, Ram A. ;
Das, Parthasarathi .
RSC ADVANCES, 2013, 3 (29) :11472-11475
[24]   COBALT(O) CATALYZED SYNTHESIS OF N-SUBSTITUTED DIHYDROPYRROLOPYRIDINES [J].
CHIUSOLI, GP ;
COSTA, M ;
REVERBERI, S ;
TERENGHI, MG .
TRANSITION METAL CHEMISTRY, 1989, 14 (03) :238-240
[25]   IMINATION OF SULFUR-CONTAINING-COMPOUNDS .26. IMINATION OF N-SUBSTITUTED TRICHLOROMETHANESULFENE AMIDES BY N-CHLORO AMIDES OF CARBOXYLIC-ACIDS [J].
KOVAL, IV ;
TARASENKO, AI ;
PANCHENKO, IS ;
MOLCHANOVA, NR .
ZHURNAL ORGANICHESKOI KHIMII, 1986, 22 (08) :1712-1715
[26]   Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-Heterobenzimidazoles [J].
Lv, Xin ;
Bao, Weiliang .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5618-5621
[27]   Copper-Catalyzed N-Arylation of Tautomerizable Heterocycles with Boronic Acids and Its Application to Synthesis of Oxygenated Carbazoles [J].
Kumar, Karampoori Anil ;
Kannaboina, Prakash ;
Jaladanki, Chaitanya K. ;
Bharatam, Prasad V. ;
Das, Parthasarathi .
CHEMISTRYSELECT, 2016, 1 (03) :601-607
[28]   Copper-Catalyzed Imino C-N Bond Formation with Aryl Boronic Acids under Aerobic Conditions [J].
Mandal, Prashant S. ;
Kumar, A. Vijay .
SYNLETT, 2016, 27 (09) :1408-1412
[29]   N-Substituted amino acids as anticorrosion additives. Part III: N-Acyl amino acids [J].
Telegdi, J. .
INTERNATIONAL JOURNAL OF CORROSION AND SCALE INHIBITION, 2016, 5 (03) :263-272
[30]   Copper-Catalyzed N-N Bond Formation by Homocoupling of Ketoximes via N-O Bond Cleavage: Facile, Mild, and Efficient Synthesis of Azines [J].
Zhao, Mi-Na ;
Liang, Hao ;
Ren, Zhi-Hui ;
Guan, Zheng-Hui .
SYNTHESIS-STUTTGART, 2012, 44 (10) :1501-1506
12345