Visible light-mediated oxidative C(sp3)-H phosphonylation for α-aminophosphonates under oxidant-free conditions

被引：80

作者：

Niu, Linbin ^{[1
]}

Wang, Shengchun ^{[1
]}

Liu, Jiamei ^{[1
]}

Yi, Hong ^{[1
]}

Liang, Xing-An ^{[1
]}

Liu, Tianyi ^{[1
]}

Lei, Aiwen ^{[1
,2
]}

机构：

[1] Wuhan Univ, IAS, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 13期

基金：

中国国家自然科学基金;

关键词：

DEHYDROGENATIVE-COUPLING REACTIONS; N-ARYL TETRAHYDROISOQUINOLINES; BOND-FORMING REACTIONS; C-H FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; BIOLOGICAL EVALUATION; EXCITED-STATE; EFFICIENT; AMINES; PHOSPHONATION;

D O I：

10.1039/c7cc09624k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An external oxidant-free synthesis of alpha-aminophosphonates by synergistically combining photocatalysis and proton-reduction catalysis is developed herein. The gram-scale experiment demonstrates the potential utility of this protocol. This study may have important implications for the functionalization of oxidant-sensitive C(sp(3))-H bonds.

引用

页码：1659 / 1662

页数：4

共 51 条

[1] Synthesis and biological evaluation of some new polyfluorinated 4-thiazolidinone and α-aminophosphonic acid derivatives [J].

Abdel-Rahman, Reda M. ;

Ali, Tarik E. .

MONATSHEFTE FUR CHEMIE, 2013, 144 (08) :1243-1252

[2] CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].

Alagiri, Kaliyamoorthy ;

Devadig, Pradeep ;

Prabhu, Kandikere R. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164

[3] Splitting Water with Cobalt [J].

Artero, Vincent ;

Chavarot-Kerlidou, Murielle ;

Fontecave, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) :7238-7266

[4] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].

Basle, Olivier ;

Li, Chao-Jun .

CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126

[5] Design, synthesis, SAR, and biological evaluation of highly potent benzimidazole-spaced phosphono-α-amino acid competitive NMDA antagonists of the AP-6 type [J].

Baudy, RB ;

Fletcher, H ;

Yardley, JP ;

Zaleska, MM ;

Bramlett, DR ;

Tasse, RP ;

Kowal, DM ;

Katz, AH ;

Moyer, JA ;

Abou-Gharbia, M .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (10) :1516-1529

[6] Visible-Light-Mediated Oxygenation Reactions using Molecular Oxygen [J].

Bian, Changliang ;

Singh, Atul K. ;

Niu, Linbin ;

Yi, Hong ;

Lei, Aiwen .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) :386-396

[7] Hydrogen Evolution Catalyzed by Cobaloximes [J].

Dempsey, Jillian L. ;

Brunschwig, Bruce S. ;

Winkler, Jay R. ;

Gray, Harry B. .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (12) :1995-2004

[8] OXIDATIVE PHOSPHONYLATION OF AROMATIC-COMPOUNDS [J].

EFFENBERGER, F ;

KOTTMANN, H .

TETRAHEDRON, 1985, 41 (19) :4171-4182

[9] THE SYNTHESIS OF ESTERS OF SUBSTITUTED AMINO PHOSPHONIC ACIDS [J].

FIELDS, EK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (06) :1528-1531

[10] Photoredox catalysis under shear using thin film vortex microfluidics [J].

Gandy, Michael N. ;

Raston, Colin L. ;

Stubbs, Keith A. .

CHEMICAL COMMUNICATIONS, 2015, 51 (55) :11041-11044

← 1 2 3 4 5 6 →