Oxidative C(SP2)-P Formation: Direct Construction of C-P Bond on Quinoxalines via Aromatic Phosphorous Oxide

被引：1

作者：

Xiong, Yunkui ^{[1
,2
]}

Zhang, Jianye ^{[1
]}

Qi, Liping ^{[2
]}

Zhang, Yu ^{[2
]}

Wang, Tao ^{[1
,2
]}

机构：

[1] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Jiangxi Prov Key Lab Chem Biol, Nanchang 330022, Jiangxi, Peoples R China

[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Jiangxi, Peoples R China

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Heterocycles⋅ Oxidative coupling; Organophosphorous compounds⋅ Quinoxaline; Synthetic methods; PALLADIUM-CATALYZED PHOSPHONATION; METAL-FREE; H BOND; DIRECT PHOSPHORYLATION; FORMING REACTIONS; ARYL MESYLATES; EFFICIENT; ACIDS; ALLENYLPHOSPHONATES; HETEROARENES;

D O I：

10.1002/slct.202004036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidative coupling has been widely used in the construction of C-C, C-N and C-S bond. Nevertheless, the method of oxidative coupling is rarely used to construct C-P bond and has not attracted enough attention. Herein, we found an innovative and simple method to construct C-P bond by oxidative coupling. Through the method, we successfully constructed the C-P bond on quinoxaline, and using this method, a series of quinoxaline derivatives were synthesized in good to excellent yield. Furthermore, the method is also suitable for large-scale production and may be used to industrial application

引用

页码：657 / 662

页数：6

共 57 条

[1] Microwave-Promoted Palladium(II)-Catalyzed C-P Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates [J].

Andaloussi, Mounir ;

Lindh, Jonas ;

Savmarker, Jonas ;

Sjoberg, Per J. R. ;

Larhed, Mats .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :13069-13074

[2] Organophosphorus π-conjugated materials [J].

Baumgartner, Thomas ;

Reau, Regis .

CHEMICAL REVIEWS, 2006, 106 (11) :4681-4727

[3] Room Temperature, Palladium-Mediated P-Arylation of Secondary Phosphine Oxides [J].

Bloomfield, Aaron J. ;

Herzon, Seth B. .

ORGANIC LETTERS, 2012, 14 (17) :4370-4373

[4] Silver-Mediated Oxidative C-H/P-H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides [J].

Chen, Yun-Rong ;

Duan, Wei-Liang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) :16754-16757

[5] Visible light-promoted C-H functionalization of ethers and electron-deficient arenes [J].

Devari, Shekaraiah ;

Shah, Bhahwal Ali .

CHEMICAL COMMUNICATIONS, 2016, 52 (07) :1490-1493

[6] Pd(II)-Catalyzed Phosphorylation of Aryl C-H Bonds [J].

Feng, Chen-Guo ;

Ye, Mengchun ;

Xiao, Kai-Jiong ;

Li, Suhua ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9322-9325

[7] Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates [J].

Fu, Wai Chung ;

So, Chau Ming ;

Kwong, Fuk Yee .

ORGANIC LETTERS, 2015, 17 (23) :5906-5909

[8] Visible-light-induced ligand-free RuCl3 catalyzed C-H phosphorylation in water [J].

Gou, Xue-Ya ;

Zhang, Bo-Sheng ;

Wang, Xin-Gang ;

Shi, Wei-Yu ;

Liu, Hong-Chao ;

An, Yang ;

Zhang, Zhe ;

Liang, Yong-Min .

CHEMICAL COMMUNICATIONS, 2020, 56 (34) :4704-4707

[9] Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C-H Bond Cleavages [J].

Graczyk, Karolina ;

Ma, Wenbo ;

Ackermann, Lutz .

ORGANIC LETTERS, 2012, 14 (16) :4110-4113

[10] Stereoselective synthesis of vinylphosphonates and phosphine oxides via silver-catalyzed phosphorylation of styrenes [J].

Gui, Qingwen ;

Hu, Liang ;

Chen, Xiang ;

Liu, Jidan ;

Tan, Ze .

CHEMICAL COMMUNICATIONS, 2015, 51 (73) :13922-13924

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