Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis

被引：110

作者：

Liao, Li-Li ^{[1
]}

Gui, Yong-Yuan ^{[1
]}

Zhang, Xiao-Bo ^{[1
]}

Shen, Guo ^{[1
]}

Liu, Hui-Dong ^{[1
]}

Zhou, Wen-Jun ^{[1
,2
]}

Li, Jing ^{[1
]}

Yu, Da-Gang ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China

[2] Neijiang Normal Univ, Coll Chem & Chem Engn, Neijiang 641112, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 14期

基金：

中国国家自然科学基金;

关键词：

VISIBLE-LIGHT PHOTOREDOX; CROSS-COUPLING REACTIONS; SINGLE-ELECTRON TRANSMETALATION; NICKEL CATALYSIS; METAL-FREE; PHOSPHINE OXIDES; H FUNCTIONALIZATION; PHENOL DERIVATIVES; FORMING REACTIONS; ACTIVATION;

D O I：

10.1021/acs.orglett.7b01561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are generated in moderate to excellent yields. This method features mild reaction Conditions, high selectivity, good functional group tolerance, wide substrate Scope, and easy scalability.

引用

页码：3735 / 3738

页数：4

共 98 条

[1]

Ahneman DT, 2016, CHEM SCI, V7, P7002, DOI [10.1039/c6sc02815b, 10.1039/C6SC02815B]

[2] Photochemical Reactions as Key Steps in Natural Product Synthesis [J].

Bach, Thorsten ;

Hehn, Joerg P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1000-1045

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

Baumgartner, Thomas ;

Reau, Regis .

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

[4] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis [J].

Beatty, Joel W. ;

Stephenson, Corey R. J. .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1474-1484

[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] Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling [J].

Cavalcanti, Livia N. ;

Molander, Gary A. .

TOPICS IN CURRENT CHEMISTRY, 2016, 374 (04)

[7]

Chen J.-R., 2016, ACCOUNTS CHEM RES, V49, P1911

[8] Nickel-Catalyzed CO/CH Cross-Coupling Reactions for CC Bond Formation [J].

Chen, Tieqiao ;

Han, Li-Biao .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (30) :8600-8602

[9] 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

[10] Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds [J].

Corce, Vincent ;

Chamoreau, Lise-Marie ;

Derat, Etienne ;

Goddard, Jean-Philippe ;

Ollivier, Cyril ;

Fensterbank, Louis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) :11414-11418

← 1 2 3 4 5 6 7 8 9 10 →