A Mild, Selective Copper-Catalyzed Oxidative Phosphonation of α-Amino Ketones

被引：95

作者：

Yang, Bin ^{[1
]}

Yang, Ting-Ting ^{[1
]}

Li, Xi-An ^{[1
]}

Wang, Jun-Jiao ^{[1
]}

Yang, Shang-Dong ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 19期

关键词：

C-H BOND; DEHYDROGENATIVE-COUPLING CDC; TERTIARY-AMINES; NITROGEN ATOM; MOLECULAR-OXYGEN; TERMINAL ALKYNES; ADJACENT; METAL; ACTIVATION; IMINES;

D O I：

10.1021/ol402355a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and selective method of simple copper-salt catalyzed phosphonation of alpha-amino carbonyl compounds to afford imidoylphosphonates is reported. This reaction system has a broad reaction scope. The convenient and environmentally benign process makes this protocol very attractive.

引用

页码：5024 / 5027

页数：4

共 77 条

[1]

Ade H., 2011, ORG LETT, V3, P313

[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] Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C-H bonds: synthesis of α-aminophosphonates under aerobic conditions [J].

Alagiri, Kaliyamoorthy ;

Devadig, Pradeep ;

Prabhu, Kandikere R. .

TETRAHEDRON LETTERS, 2012, 53 (12) :1456-1459

[4] Organocatalytic Asymmetric Synthesis of Organophosphorus Compounds [J].

Albrecht, Lukasz ;

Albrecht, Anna ;

Krawczyk, Henryk ;

Jorgensen, Karl Anker .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :28-48

[5] Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors [J].

Alexandre, Francois-Rene ;

Amador, Agnes ;

Bot, Stephanie ;

Caillet, Catherine ;

Convard, Thierry ;

Jakubik, Jocelyn ;

Musiu, Chiara ;

Poddesu, Barbara ;

Vargiu, Luana ;

Liuzzi, Michel ;

Roland, Arlene ;

Seifer, Maria ;

Standring, David ;

Storer, Richard ;

Dousson, Cyril B. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :392-395

[6]

Allen DW, 2010, SPR-ORGANOPHOS CHEM, V39, P1, DOI 10.1039/9781849730839-00001

[7] Catalytic synthesis of phosphines and related compounds [J].

Baillie, C ;

Xiao, JL .

CURRENT ORGANIC CHEMISTRY, 2003, 7 (05) :477-514

[8] Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].

Basle, Olivier ;

Li, Chao-Jun .

GREEN CHEMISTRY, 2007, 9 (10) :1047-1050

[9] Aerobic and Electrochemical Oxidative Cross-Dehydrogenative-Coupling (CDC) Reaction in an Imidazolium-Based Ionic Liquid [J].

Basle, Olivier ;

Borduas, Nadine ;

Dubois, Pauline ;

Chapuzet, Jean Marc ;

Chan, Tak-Hang ;

Lessard, Jean ;

Li, Chao-Jun .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) :8162-8166

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

Basle, Olivier ;

Li, Chao-Jun .

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

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