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
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
收藏
页码:159 / 162
页数:4
相关论文
共 46 条
[11]   Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms [J].
Ghobrial, Michael ;
Schnuerch, Michael ;
Mihovilovic, Marko D. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21) :8781-8793
[12]   Eosin Y Catalyzed Visible Light Oxidative C-C and C-P bond Formation [J].
Hari, Durga Prasad ;
Koenig, Burkhard .
ORGANIC LETTERS, 2011, 13 (15) :3852-3855
[13]  
Jones K.M., 2011, CHEMCATCHEM IN PRESS, DOI [10.1002/cctc.201100324, DOI 10.1002/CCTC.201100324]
[14]   Catalytic Oxidative Coupling Reactions for the Formation of Carbon-Carbon Bonds without Carbon-Metal Intermediates [J].
Klussmann, Martin ;
Sureshkumar, Devarajulu .
SYNTHESIS-STUTTGART, 2011, (03) :353-369
[15]   FeCl3-Catalyzed Oxidative Allylation of sp2 and sp3 C-H Bond Adjacent to a Nitrogen Atom: Easy Access to Homoallyl Tertiary Amines [J].
Kumaraswamy, Gullapalli ;
Murthy, Akula Narayana ;
Pitchaiah, Arigala .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (11) :3916-3919
[16]   Understanding and exploiting C-H bond activation [J].
Labinger, JA ;
Bercaw, JE .
NATURE, 2002, 417 (6888) :507-514
[17]   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
[18]   Studies on Cu-catalyzed asymmetric alkynylation of tetrahydroisoquinoline derivatives [J].
Li, ZP ;
MacLeod, PD ;
Li, CJ .
TETRAHEDRON-ASYMMETRY, 2006, 17 (04) :590-597
[19]   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
[20]   CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds [J].
Li, ZP ;
Li, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6968-6969