Potassium iodide catalyzed simultaneous C3-formylation and N-aminomethylation of indoles with 4-substituted-N,N-dimethylanilines

被引：58

作者：

Li, Lan-Tao ^{[1
]}

Li, Hong-Ying ^{[1
]}

Xing, Li-Juan ^{[1
]}

Wen, Li-Juan ^{[1
]}

Wang, Peng ^{[1
]}

Wang, Bin ^{[1
]}

机构：

[1] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300071, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 48期

基金：

中国国家自然科学基金;

关键词：

C-H BOND; DEHYDROGENATIVE COUPLING REACTIONS; STUDIEN ZUM ABLAUF; BETA-KETO-ESTERS; TERTIARY-AMINES; OXIDATIVE CYANATION; HYDROGEN-PEROXIDE; DIRECT FUNCTIONALIZATION; MOLECULAR-OXYGEN; ACTIVATION;

D O I：

10.1039/c2ob26636a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot dual functionalization of indoles has been developed. The simultaneous C3-formylation and N-aminomethylation of indoles can be achieved using readily available potassium iodide as a catalyst and tert-butyl peroxybenzoate as a co-oxidant.

引用

页码：9519 / 9522

页数：4

共 67 条

[1] Selective Ruthenium-Catalyzed N-Alkylation of Indoles by Using Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Mevius, Kathleen ;

Neubert, Lorenz ;

Tillack, Annegret ;

Williams, Jonathan M. J. ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (12) :3590-3593

[2] 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

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

Campos, Kevin R. .

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

[5] 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

[6] Bu4NI-Catalyzed C-O Bond Formation by Using a Cross-Dehydrogenative Coupling (CDC) Reaction [J].

Chen, Long ;

Shi, Erbo ;

Liu, Zhaojun ;

Chen, Shulin ;

Wei, Wei ;

Li, Hong ;

Xu, Kai ;

Wan, Xiaobing .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (15) :4085-4089

[7] Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].

Chen, Shulin ;

Xu, Yuan ;

Wan, Xiaobing .

ORGANIC LETTERS, 2011, 13 (23) :6152-6155

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

CHIBA, T ;

TAKATA, Y .

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

[9] A Metal-Free Oxidative Esterification of the Benzyl C?H Bond [J].

Feng, Jie ;

Liang, Shuai ;

Chen, Shan-Yong ;

Zhang, Ji ;

Fu, Song-Sen ;

Yu, Xiao-Qi .

ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (07) :1287-1292

[10] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles [J].

Ferreira, EM ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9578-9579

← 1 2 3 4 5 6 7 →