Oxidative Coupling of Tertiary Amines: Scope, Mechanism and Challenges

被引：107

作者：

Jones, Kevin M. ^{[1
]}

Klussmann, Martin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

SYNLETT | 2012年 / 02期

关键词：

oxidation; cross-coupling; catalysis; mechanism; C-H functionalization; SP(3) C-H; CARBON BOND FORMATION; NITROGEN ATOM; SODIUM-CYANIDE; TETRAHYDROISOQUINOLINE DERIVATIVES; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; ACTIVATION; CYANATION; ADJACENT;

D O I：

10.1055/s-0031-1290117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This article highlights the current scope of oxidative coupling reactions of tertiary amines. Emphasis has been placed on recent synthetic and mechanistic studies and suggests potential areas of improvement for the future.

引用

页码：159 / 162

页数：4

共 46 条

[1]

[Anonymous], 2010, CHEM REV, V110, P575

[2]

Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a

[3] Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent [J].

Boess, Esther ;

Sureshkumar, Devarajulu ;

Sud, Abhishek ;

Wirtz, Cornelia ;

Fares, Christophe ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8106-8109

[4] ANODIC CYANATION OF TERTIARY ALIPHATIC AND HETEROCYCLIC AMINES [J].

CHIBA, T ;

TAKATA, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (18) :2973-2977

[5] Benzoyl peroxide (BPO)-promoted oxidative trifluoromethylation of tertiary amines with trimethyl(trifluoromethyl)silane [J].

Chu, Lingling ;

Qing, Feng-Ling .

CHEMICAL COMMUNICATIONS, 2010, 46 (34) :6285-6287

[6] CuBr-Catalyzed Oxidative Difluoromethylation of Tertiary Amines with Difluoroenol Silyl Ethers [J].

Chu, Lingling ;

Zhang, Xingang ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2009, 11 (10) :2197-2200

[7] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].

Colby, Denise A. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

CHEMICAL REVIEWS, 2010, 110 (02) :624-655

[8] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].

Condie, Allison G. ;

Gonzalez-Gomez, Jose C. ;

Stephenson, Corey R. J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+

[9] The development of a Selectfluor®-mediated oxidative Mannich reaction [J].

Daniels, Matthew H. ;

Hubbs, Jed .

TETRAHEDRON LETTERS, 2011, 52 (28) :3543-3546

[10] Catalytic Carbene Insertion into C-H Bonds [J].

Doyle, Michael P. ;

Duffy, Richard ;

Ratnikov, Maxim ;

Zhou, Lei .

CHEMICAL REVIEWS, 2010, 110 (02) :704-724

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