Direct phosphonation of quinoxalin-2(1H)-ones under transition-metal-free conditions

被引：212

作者：

Gao, Ming ^{[1
,2
]}

Li, Yi ^{[1
,2
]}

Xie, Lijuan ^{[1
,2
]}

Chauvinabc, Remi ^{[1
,2
,3
,4
]}

Cui, Xiuling ^{[1
,2
]}

机构：

[1] Huaqiao Univ, Engn Res Ctr Mol Med, Key Lab Xiamen Marine & Gene Drugs, Minist Educ,Inst Mol Med, Xiamen 361021, Peoples R China

[2] Huaqiao Univ, Sch Biomed Sci, Xiamen 361021, Peoples R China

[3] CNRS, Chim Coordinat Lab, 205 Route Narbonne,BP 44099, F-31077 Toulouse 4, France

[4] Univ Toulouse, UPS, INPT, F-31077 Toulouse 4, France

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 13期

关键词：

DIALKYL H-PHOSPHONATES; CARBON-PHOSPHORUS FUNCTIONALIZATION; PALLADIUM-CATALYZED PHOSPHONATION; P BOND FORMATION; C-P; REGIOSELECTIVE PHOSPHONATION; PHOSPHINE OXIDES; ACIDS; ARYL; DIPHENYLPHOSPHINE;

D O I：

10.1039/c5cc08049e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A direct C-H bond phosphonation of quinoxalin-2(1H)-ones with H-phosphonates, H-phosphinates or H-phosphine oxides has been developed. A wide variety of heteroaryl phosphonates were obtained in up to 92% yield for 20 examples under transition-metal-free conditions. This protocol tolerates a broad scope of substrates and features practicality, high efficiency, environmental friendliness and atom economy.

引用

页码：2846 / 2849

页数：4

共 50 条

[11] Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates [J].

Gao, Yuxing ;

Wang, Gang ;

Chen, Lu ;

Xu, Pengxiang ;

Zhao, Yufen ;

Zhou, Yongbo ;

Han, Li-Biao .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :7956-+

[12] Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes [J].

Han, LB ;

Zhang, C ;

Yazawa, H ;

Shimada, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5080-5081

[13] Eosin Y Catalyzed Visible Light Oxidative C-C and C-P bond Formation [J].

Hari, Durga Prasad ;

Koenig, Burkhard .

ORGANIC LETTERS, 2011, 13 (15) :3852-3855

[14]

HIRAO T, 1981, SYNTHESIS-STUTTGART, P56

[15] PALLADIUM-CATALYZED NEW CARBON-PHOSPHORUS BOND FORMATION [J].

HIRAO, T ;

MASUNAGA, T ;

YAMADA, N ;

OHSHIRO, Y ;

AGAWA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (03) :909-913

[16] PEPTIDE-SYNTHESIS CATALYZED BY AN ANTIBODY CONTAINING A BINDING-SITE FOR VARIABLE AMINO-ACIDS [J].

HIRSCHMANN, R ;

SMITH, AB ;

TAYLOR, CM ;

BENKOVIC, PA ;

TAYLOR, SD ;

YAGER, KM ;

SPRENGELER, PA ;

BENKOVIC, SJ .

SCIENCE, 1994, 265 (5169) :234-237

[17] Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites [J].

Hou, Chaodong ;

Ren, Yunlai ;

Lang, Rui ;

Hu, Xiaoxue ;

Xia, Chungu ;

Li, Fuwei .

CHEMICAL COMMUNICATIONS, 2012, 48 (42) :5181-5183

[18] Copper-Catalyzed Decarboxylative C-P Cross-Coupling of Alkynyl Acids with H-Phosphine Oxides: A Facile and Selective Synthesis of (E)-1-Alkenylphosphine Oxides [J].

Hu, Gaobo ;

Gao, Yuxing ;

Zhao, Yufen .

ORGANIC LETTERS, 2014, 16 (17) :4464-4467

[19]

Jeon SO, 2012, J MATER CHEM, V22, P7239, DOI [10.1039/c2jm30742a, 10.1039/c2jm.30742a]

[20] BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].

KAFARSKI, P ;

LEJCZAK, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215

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