Electrochemical Oxidation-Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer

被引：29

作者：

Yang, Jianjing ^{[1
]}

Sun, Xue ^{[1
]}

Yan, Kelu ^{[1
]}

Sun, Hongzhao ^{[1
]}

Sun, Shuai ^{[1
]}

Jia, Xiaoyu ^{[1
]}

Zhang, Fanjun ^{[1
]}

Wen, Jiangwei ^{[1
]}

机构：

[1] Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Green Nat Prod & Pharmaceut Intermediates, Jining, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Electrochemical; Oxyphosphorylation; Alkenes and alkynes; Water; Hydrogen atom transfer; H-PHOSPHINE OXIDES; CATALYZED DIRECT OXYPHOSPHORYLATION; BETA-KETOPHOSPHINE OXIDES; AEROBIC OXYPHOSPHORYLATION; RADICAL OXYPHOSPHORYLATION; PHOSPHONATES; STYRENES; FUNCTIONALIZATION; ELECTROSYNTHESIS; PHOSPHORYLATION;

D O I：

10.1002/adsc.202200421

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A metal- and exogenous-oxidant-free oxidation-induced oxyphosphorylation of alkenes and alkynes with water for beta-ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible with a wide range of alkenes, alkynes, and diarylphosphorus derivatives, and enables the gramscale synthesis of beta-ketophosphonates. The mechanistic study revealed that the P radicals were generated via hydrogen atom transfer (HAT) event jointly mediated by tetrabutylammonium acetate and anode oxidation process.

引用

页码：2735 / 2740

页数：6

共 48 条

[1]

[Anonymous], 2013, ANGEW CHEM, V125, P4064

[2] Synthesis of a β-Ketophosphonate Bioisostere of UDP-N-acetylglucosamine [J].

Auberger, Nicolas ;

Gravier-Pelletier, Christine ;

Le Merrer, Yves .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (20) :3323-3326

[3] Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides [J].

Bai, Ya ;

Liu, Nian ;

Wang, Shutao ;

Wang, Siyu ;

Ning, Shulin ;

Shi, Lingling ;

Cui, Lili ;

Zhang, Zhuoqi ;

Xiang, Jinbao .

ORGANIC LETTERS, 2019, 21 (17) :6835-6838

[4] Oxidation of secondary alcohols and ethers by dimethyldioxirane [J].

Baumstark, AL ;

Kovac, F ;

Vasquez, PC .

CANADIAN JOURNAL OF CHEMISTRY, 1999, 77 (03) :308-312

[5] Metal-free oxidative phosphinylation of aryl alkynes to β-ketophosphine oxides via visible-light photoredox catalysis [J].

Bu, Mei-jie ;

Lu, Guo-ping ;

Cai, Chun .

CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (02) :413-416

[6] Acetonitrile-dependent oxyphosphorylation: A mild one-pot synthesis of β-ketophosphonates from alkenyl acids or alkenes [J].

Chen, Xi ;

Chen, Xiaolan ;

Li, Xu ;

Qu, Chen ;

Qu, Lingbo ;

Bi, Wenzhu ;

Sun, Kai ;

Zhao, Yufen .

TETRAHEDRON, 2017, 73 (17) :2439-2446

[7] Peroxides as "Switches" of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates [J].

Chen, Xiao-Lan ;

Li, Xu ;

Qu, Ling-Bo ;

Tang, Yu-Chun ;

Mai, Wen-Peng ;

Wei, Dong-Hui ;

Bi, Wen-Zhu ;

Duan, Li-Kun ;

Sun, Kai ;

Chen, Jian-Yu ;

Ke, Dian-Dian ;

Zhao, Yu-Fen .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8407-8416

[8] A one-pot strategy to synthesize β-ketophosphonates: silver/copper catalyzed direct oxyphosphorylation of alkynes with H-phosphonates and oxygen in the air [J].

Chen, Xin ;

Li, Xu ;

Chen, Xiao-Lan ;

Qu, Ling-Bo ;

Chen, Jian-Yu ;

Sun, Kai ;

Liu, Zhi-Dong ;

Bi, Wen-Zhu ;

Xia, Ying-Ya ;

Wu, Hai-Tao ;

Zhao, Yu-Fen .

CHEMICAL COMMUNICATIONS, 2015, 51 (18) :3846-3849

[9] METAL SALTS AND COMPLEXES OF DIALKOXYPHOSPHONYLACETYLMETHANIDE IONS [J].

COTTON, FA ;

SCHUNN, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (16) :2394-&

[10] Electrochemical Oxidative Dehydrogenative Phosphorylation of N-Heterocycles with P(O)-H Compounds in Imidazolium-Based Ionic Liquid [J].

Dong, Xiaojuan ;

Wang, Ruige ;

Jin, Weiwei ;

Liu, Chenjiang .

ORGANIC LETTERS, 2020, 22 (08) :3062-3066

← 1 2 3 4 5 →