Copper-Catalyzed Domino Oxidation-Acyloxylation Reaction of 2-Arylpyridines with Aldehydes or Methylarenes

被引：36

作者：

Bian, Yong-Jun ^{[1
]}

Xiang, Chang-Bing ^{[1
]}

Chen, Zhi-Ming ^{[1
]}

Huang, Zhi-Zhen ^{[1
,2
,3
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

SYNLETT | 2011年 / 16期

基金：

中国国家自然科学基金;

关键词：

C-H activation; copper catalysis; domino reaction; acyloxylation; oxidation; TERT-BUTYL HYDROPEROXIDE; O BOND FORMATION; C-H BONDS; CASCADE REACTIONS; ARYL KETONES; ACTIVATION; FUNCTIONALIZATION; EFFICIENT; ACIDS;

D O I：

10.1055/s-0030-1261224

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino oxidation-acyloxylation reaction of 2-arylpyridines with aldehydes or methylarenes under the catalysis of Cu(OAc)(2) has been developed. The strategy via C-H bond functionalization has the advantages of good functional-group tolerance, high ortho regioselectivity and no need of any ligand or additive.

引用

页码：2407 / 2409

页数：3

共 27 条

[1] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[2] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

[3] Asymmetric organocatalytic domino reactions [J].

Enders, Dieter ;

Grondal, Christoph ;

Huettl, Matthias R. M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581

[4]

Grondal C, 2010, NAT CHEM, V2, P167, DOI [10.1038/NCHEM.539, 10.1038/nchem.539]

[5] Palladium-catalyzed acetoxylation of sp3 C-H bonds using molecular oxygen [J].

Jiang, Huanfeng ;

Chen, Huoji ;

Wang, Azhong ;

Liu, Xiaohang .

CHEMICAL COMMUNICATIONS, 2010, 46 (38) :7259-7261

[6] Regioselectivity in palladium-catalyzed C-H activation/oxygenation reactions [J].

Kalyani, D ;

Sanford, MS .

ORGANIC LETTERS, 2005, 7 (19) :4149-4152

[7] Cu-facilitated C-O bond formation using N-hydroxyphthalimide:: Efficient and selective functionalization of benzyl and allylic C-H bonds [J].

Lee, Ji Min ;

Park, Eun Ju ;

Cho, Seung Hwan ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (25) :7824-+

[8] CuCl catalyzed oxidation of aldehydes to carboxylic acids with aqueous tert-butyl hydroperoxide under mild conditions [J].

Mannam, Sreedevi ;

Sekar, G. .

TETRAHEDRON LETTERS, 2008, 49 (06) :1083-1086

[9] Regioselective C-H Activation and Sequential C-C and C-O Bond Formation Reactions of Aryl Ketones Promoted by an Yttrium Carbene [J].

Mills, David P. ;

Soutar, Lyndsay ;

Lewis, William ;

Blake, Alexander J. ;

Liddle, Stephen T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) :14379-14381

[10] Cascade reactions in total synthesis [J].

Nicolaou, K. C. ;

Edmonds, David J. ;

Bulger, Paul G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7134-7186

← 1 2 3 →