The copper-catalyzed radical aminophosphinoylation of maleimides with anilines and diarylphosphine oxides

被引：14

作者：

Xu, Yaling ^{[1
]}

Zhou, Xueying ^{[1
]}

Chen, Luya ^{[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 CHEMISTRY FRONTIERS | 2022年 / 9卷 / 09期

基金：

中国国家自然科学基金;

关键词：

C-P; ENAMIDES; ACCESS; AMINES; HYDROPHOSPHINYLATION; PHOSPHORYLATION; YNAMIDES; ALKENES; FACILE; BONDS;

D O I：

10.1039/d2qo00184e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper-catalyzed radical multi-component coupling of maleimides, anilines, and diarylphosphine oxides has been realized, providing the rapid synthesis of a library of aminophosphinoylated maleimides, with the formation of C-N and C-P bonds. The remarkable feature of the current multi-component reaction was that five clinical drug molecules containing sulfonamide and arylamine functional groups underwent chemo-selective radical vinylphosphinoylation to access sterically congested products. Most impressively, this transformation worked on a wide range of substrates and showed good functional group tolerance.

引用

页码：2471 / 2476

页数：6

共 38 条

[1] Direct Enamido C(sp2)-H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates [J].

Cao Hao-Qiang ;

Liu Hao-Nan ;

Liu Zhe-Yuan ;

Qiao Bao-Kun ;

Zhang Fa-Guang ;

Ma Jun-An .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (24) :5515-5521

[2] Rh-Catalyzed Asymmetric Hydrogenation of (Z)-β-Phosphorylated Enamides: Highly Enantioselective Access to β-Arninophosphines [J].

Du, Hong-Quan ;

Hu, Xiang-Ping .

ORGANIC LETTERS, 2019, 21 (22) :8921-8924

[3] Highly Regio- and Stereoselective Nickel-Catalyzed Addition of Dialkyl Phosphites to Ynamides: an Efficient Synthesis of β-Aminovinylphosphonates [J].

Fadel, Antoine ;

Legrand, Frederic ;

Evano, Gwilherm ;

Rabasso, Nicolas .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :263-267

[4] Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates [J].

Fraser, Jamie ;

Wilson, Laura J. ;

Blundell, Rebecca K. ;

Hayes, Christopher J. .

CHEMICAL COMMUNICATIONS, 2013, 49 (79) :8919-8921

[5] A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles [J].

Gao, Yuzhen ;

Lu, Guozhang ;

Zhang, Pengbo ;

Zhang, Liangliang ;

Tang, Guo ;

Zhao, Yufen .

ORGANIC LETTERS, 2016, 18 (06) :1242-1245

[6] Copper-Catalyzed Phosphonation-Annulation Approaches to the Synthesis of β-Phosphonotetrahydrofurans Involving C-P and C-O Bonds Formation [J].

Gao, Yuzhen ;

Li, Xueqin ;

Chen, Weizhu ;

Tang, Guo ;

Zhao, Yufen .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (22) :11398-11406

[7] Cu(I)/Fe(III)-Catalyzed C-P cross-coupling of styrenes with H-phosphine oxides: a facile and selective synthesis of alkenylphosphine oxides and β-ketophosphonates [J].

Gu, Jian ;

Cai, Chun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (19) :4226-4230

[8] Boron Lewis Acid-Catalyzed Hydrophosphinylation of N-Heteroaryl-Substituted Alkenes with Secondary Phosphine Oxides [J].

Han, Jimin ;

Kim, Jongwon ;

Lee, Jaehoo ;

Kim, Younghun ;

Lee, Sarah Yunmi .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) :15476-15487

[9] Regio- and Stereoselective Hydrophosphorylation of Ynamides for the Synthesis of β-Aminovinylphosphine Oxides [J].

Huang, Hai ;

Zhu, Hongjun ;

Kang, Jun Yong .

ORGANIC LETTERS, 2018, 20 (09) :2778-2781

[10] A simple and effective synthesis of activated vinylphosphonates from 3-methoxy-2-diethoxyphosphorylacrylate [J].

Janecki, Tomasz ;

Albrecht, Anna ;

Koszuk, Jacek F. ;

Modranka, Jakub ;

Slowak, Dominika .

TETRAHEDRON LETTERS, 2010, 51 (17) :2274-2276

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