Thieme Chemistry Journal Awardees - Where Are They Now? Aerobic Oxidative Coupling of Tertiary Amines with Silyl Enolates and Ketene Acetals

被引：62

作者：

Sureshkumar, Devarajulu ^{[1
]}

Sud, Abhishek ^{[1
]}

Klussmann, Martin ^{[1
]}

机构：

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

来源：

SYNLETT | 2009年 / 10期

关键词：

amines; C-H bond functionalization; copper; oxidative cross-coupling; oxidations; SP(3) C-H; CARBON BOND FORMATION; MOLECULAR-OXYGEN; SODIUM-CYANIDE; ACTIVATION; CYANATION; TETRAHYDROISOQUINOLINES; CYTOCHROME-P-450; ADJACENT; NITROGEN;

D O I：

10.1055/s-0029-1217336

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclic tertiary amines can be oxidatively coupled with a variety of silyl enol ethers or ketene acetals to furnish tertiary Mannich bases. The reactions are catalyzed by simple copper salts employing elemental oxygen as the oxidant.

引用

页码：1558 / 1561

页数：4

共 25 条

[1] 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

[2] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].

Campos, Kevin R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084

[3] The oxidative Mannich reaction catalyzed by dirhodium caprolactamate [J].

Catino, AJ ;

Nichols, JM ;

Nettles, BJ ;

Doyle, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (17) :5648-5649

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

CHIBA, T ;

TAKATA, Y .

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

[5] REDOX-INDUCED RADICAL AND RADICAL IONIC CARBON-CARBON BOND-FORMING REACTIONS [J].

DALKO, PI .

TETRAHEDRON, 1995, 51 (28) :7579-7653

[6] Enantioselective organocatalytic singly occupied molecular orbital activation:: The enantioselective α-enolation of aldehydes [J].

Jang, Hye-Young ;

Hong, Jun-Bae ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (22) :7004-+

[7] Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage [J].

Kakiuchi, Fumitoshi ;

Kochi, Takuya .

SYNTHESIS-STUTTGART, 2008, (19) :3013-3039

[8] Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].

Li, Chao-Jun .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344

[9] Cu-catalyzed cross-dehydrogenative coupling:: A versatile strateav for C-C bond formations via the oxidative activation of sp3 C-H bonds [J].

Li, Zhiping ;

Bohle, D. Scott ;

Li, Chao-Jun .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) :8928-8933

[10] Highly efficient CuBr-catalyzed cross-dehydrogenative coupling (CDC) between tetrahydroisoquinolines and activated methylene compounds [J].

Li, ZP ;

Li, CJ .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) :3173-3176

← 1 2 3 →