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

被引:112
作者
Liu, Songbai [1 ]
Yu, Ying [1 ]
Liebeskind, Lanny S. [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
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
[31]   Copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates for the synthesis of 3-aryl-4-pyrrolin-2-ones [J].
Song, Xiao-Qing ;
Qiang, Xiao-Qi ;
Hu, Zi-Jun ;
Lyu, Xinyu ;
Tan, Sheng ;
Yao, Changsheng ;
Sun, Yong-Qiang ;
Miao, Chun-Bao ;
Yang, Hai-Tao .
CHEMICAL COMMUNICATIONS, 2023, 59 (35) :5225-5228
[32]   Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines [J].
Zhang, Di ;
Zhang, Da-Ming ;
Xu, Guang-Yang ;
Sun, Jiang-Tao .
CHINESE CHEMICAL LETTERS, 2015, 26 (03) :301-303
[33]   Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines [J].
Di Zhang ;
Da-Ming Zhang ;
Guang-Yang Xu ;
Jiang-Tao Sun .
Chinese Chemical Letters, 2015, (03) :301-303
[34]   Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes [J].
van Vliet, Kaj M. ;
Polak, Lara H. ;
Siegler, Maxime A. ;
van der Vlugt, Jarl Ivar ;
Guerra, Celia Fonseca ;
de Bruin, Bas .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (38) :15240-15249
[35]   IMINATION OF SULFUR-CONTAINING-COMPOUNDS .23. EFFECT OF ACIDIC PROPERTIES OF N-SUBSTITUTED SULFENYLAMIDES ON THEIR IMINATION BY SODIUMCHLOROAMIDES OF SULFO ACIDS [J].
KOVAL, IV ;
OLEINIK, TG ;
TARASENKO, AI ;
KREMLEV, MM .
ZHURNAL ORGANICHESKOI KHIMII, 1985, 21 (12) :2578-2587
[36]   Copper-Catalyzed N-Arylation of Sulfonamides with Boronic Acids in Water under Ligand-Free and Aerobic Conditions [J].
Nasrollahzadeh, Mahmoud ;
Ehsani, Ali ;
Maham, Mehdi .
SYNLETT, 2014, 25 (04) :505-508
[37]   Synthesis of α-Ketoamides by Copper-Catalyzed Reactions of Phenylacetic Acids with N,N-Dialkylformamides [J].
Zhang, Lanping ;
Pu, Junnan ;
Ren, Jiayu ;
Li, Zhengkai ;
Xiang, Haifeng ;
Zhou, Xiangge .
SYNTHETIC COMMUNICATIONS, 2015, 45 (16) :1848-1856
[38]   KINETICS OF THE ACID-CATALYZED HYDROLYSIS OF N-SUBSTITUTED HYDROXAMIC ACIDS [J].
TANDON, SG ;
GHOSH, KK .
BULLETIN DES SOCIETES CHIMIQUES BELGES, 1982, 91 (05) :398-398
[39]   Palladium-Catalyzed Preparation of N-Substituted Benz[c,d]indol-2-imines and N-Substituted Amino-1-naphthylamides [J].
Zhang, Yuan ;
Liu, Tongda ;
Liu, Li ;
Guo, Haiyang ;
Zeng, Heyang ;
Bi, Wei ;
Qiu, Guanyinsheng ;
Gao, Wei ;
Ran, Xin ;
Yang, Long ;
Du, Guanben ;
Zhang, Lianpeng .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13) :8515-8524
[40]   Copper(II)-catalyzed oxidation of N-substituted isoindolinones to the corresponding phthalimides [J].
Luzzio, Frederick A. ;
Ghosh, Shramana ;
Adjei, Bernard L. .
ARKIVOC, 2024,