Oxidative Aminoarylselenation of Maleimides via Copper-Catalyzed Four-Component Cross-Coupling

被引：37

作者：

Gao, Xue ^{[1
]}

Tang, Liyang ^{[1
]}

Huang, Lehao ^{[1
]}

Huang, Zu-Sheng ^{[1
]}

Ma, Yunfei ^{[1
]}

Wu, Ge ^{[1
,2
]}

机构：

[1] Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou 325035, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; ELEMENTAL SULFUR; ARYL IODIDES; HYDROSELENATION; ALKYNES; BOND; SE; FUNCTIONALIZATION; SULFIDES; SELENIUM;

D O I：

10.1021/acs.orglett.8b03980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of copper-catalyzed four-component coupling reaction of aryl iodides, Se powder, secondary amines, and maleimides is developed. This reaction provides an efficient and concise route to access amino-arylselenated maleimides via double C-Se bonds and C-N bond formation. The appealing features of this transformation are the use of Se powder as a selenating reagent, a green catalytic system, a wide range of substrate scope, and late-stage selenation of bioactive compounds.

引用

页码：745 / 748

页数：4

共 50 条

[1] Copper-Catalyzed Oxidative Cross-Coupling of Sulfoximines and Alkynes
Wang, Long
Huang, He
Priebbenow, Daniel L.
Pan, Fang-Fang
Bolm, Carsten
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (12) : 3478 - 3480
[2] Recent Advances in Copper-Catalyzed Oxidative Cross-Coupling Chemistry
Maheswari, C. Uma
Kumar, Gadde S.
Reddy, Kallu R.
CURRENT ORGANIC CHEMISTRY, 2016, 20 (05) : 512 - 579
[3] Four-Component Reaction for the Synthesis of Indolizines by Copper-Catalyzed Aerobic Oxidative Dehydrogenative Aromatization
Xu, Juanfang
Hu, Huayou
Liu, Yun
Wang, Xiang
Kan, Yuhe
Wang, Chao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (02) : 257 - 261
[4] Copper-catalyzed four-component coupling between aldehydes, amines, alkynes, and carbon dioxide
Yoo, Woo-Jin
Li, Chao-Jun
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (10) : 1503 - 1506
[5] Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling
Arlow, Sophie I.
Hartwig, John F.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4567 - 4572
[6] Copper-Catalyzed Cross-Coupling of Arylacetylenes with Bromodifluoroacetamides
Hu, Guo-Qin
Yao, Li-Wei
Gui, Shu-Sheng
Geng, Chuang
Zhang, Wen-Yan
Liu, Jing-Hui
Zhao, Bin
SYNLETT, 2022, 33 (06) : 594 - 598
[7] Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes
Hojoh, Kentaro
Shido, Yoshinori
Nagao, Kazunori
Mori, Seiji
Ohmiya, Hirohisa
Sawamura, Masaya
TETRAHEDRON, 2015, 71 (37) : 6519 - 6533
[8] Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones
Das, Arindam
Wang, Dong
Belhomme, Marie-Charlotte
Szabo, Kalman J.
ORGANIC LETTERS, 2015, 17 (19) : 4754 - 4757
[9] Copper-Catalyzed Sulfinyl Cross-Coupling Reaction of Sulfinamides
Kou, Mengting
Wei, Ziqiang
Li, Zhen
Xu, Bin
ORGANIC LETTERS, 2022, 24 (46) : 8514 - 8519
[10] Recent progress in copper-catalyzed cross-coupling reactions
Deng, W
Liu, L
Guo, QX
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (02) : 150 - 165

← 1 2 3 4 5 →