Recent advancements in dehydrogenative cross coupling reactions for C-C bond formation

被引：142

作者：

Varun, Begur Vasanthkumar ^{[1
]}

Dhineshkumar, Jayaraman ^{[1
]}

Bettadapur, Kiran R. ^{[1
]}

Siddaraju, Yogesh ^{[1
]}

Alagiri, Kaliyamoorthy ^{[2
]}

Prabhu, Kandikere Ramaiah ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

[2] Indian Inst Sci Educ & Res, Sch Chem, CET Campus, Thiruvananthapuram, Kerala, India

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 09期

关键词：

CDC; C-HC-H functionalization; C-C bond formation; Oxidative coupling; Radical reactions; CATALYZED OXIDATIVE CYANATION; H BOND; TERTIARY-AMINES; TRANSITION-METAL; XANTHONE FORMATION; HYDROGEN-PEROXIDE; FORMING REACTIONS; MOLECULAR-OXYGEN; C(SP(3))-H BONDS; TERMINAL ALKYNES;

D O I：

10.1016/j.tetlet.2017.01.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A significant number of reactions have appeared in the literature regarding cross dehydrogenative coupling (CDC) reactions over the years. This review aims to cover the advances in the area of C-C bond formations via CDC reactions in the last six years (2011-2016). For the sake of brevity, the review has been subdivided into four major parts (i) sp(3) - sp(3), (ii) sp(3) - sp(2), (iii) sp(2) - sp(2) and (iv) spa/sp(2) - sp bond forming reactions. The reactions are discussed based on the principal catalyst system used, i.e. metal based, non-metal based or photocatalyst. Wherever necessary, the uniqueness of the methods has been shown by highlighting the substrate scope, along with proposed mechanisms. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：803 / 824

页数：22

共 135 条

[1] 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

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3]

[Anonymous], 2014, ALL NOBEL PRIZES CHE

[4] Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes [J].

Antonchick, Andrey P. ;

Burgmann, Lars .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3267-3271

[5] 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

[6] 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

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

Basle, Olivier ;

Li, Chao-Jun .

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

[8] Bond dissociation energies of organic molecules [J].

Blanksby, SJ ;

Ellison, GB .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263

[9]

Bruce PY, 2004, ORGANIC CHEM

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

Campos, Kevin R. .

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

← 1 2 3 4 5 6 7 8 9 10 →