Palladium-Catalyzed Aerobic Oxidative Cyclization of N-Aryl lmines: lndole Synthesis from Anilines and Ketones

被引：303

作者：

Wei, Ye ^{[1
]}

Deb, Indubhusan ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 22期

基金：

新加坡国家研究基金会;

关键词：

C-H BOND; AROMATIC IMINES; INDOLES; ACTIVATION; ALKYNES; DIOXYGEN; OXIDANT; HECK;

D O I：

10.1021/ja3030824

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report here an operationally simple, palladium-catalyzed cyclization reaction of N-aryl imines, affording indoles via the oxidative linkage of two C-H bonds under mild conditions using molecular oxygen as the sole oxidant. The process allows quick and atom-economical assembly of indole rings from inexpensive and readily available anilines and ketones and tolerates a broad range of functional groups.

引用

页码：9098 / 9101

页数：4

共 52 条

[1] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (14) :3123-3125

[2] [RuCl3(H2O)n]-catalyzed direct arylations [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Born, Robert .

TETRAHEDRON, 2008, 64 (26) :6115-6124

[3] Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].

Ackermann, Lutz ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :764-767

[4] Carboxylate-Assisted Ruthenium-Catalyzed Direct Alkylations of Ketimines [J].

Ackermann, Lutz ;

Hofmann, Nora ;

Vicente, Ruben .

ORGANIC LETTERS, 2011, 13 (07) :1875-1877

[5]

AKERMARK B, 1975, J ORG CHEM, V40, P1365, DOI 10.1021/jo00897a048

[6] Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends [J].

Albrecht, Martin .

CHEMICAL REVIEWS, 2010, 110 (02) :576-623

[7]

[Anonymous], A provisional patent application of this work has been filed, application no., Patent No. 61577528

[8] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].

Bernini, Roberta ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio ;

Cacchi, Sandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081

[9] Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[10] Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].

Campbell, Alison N. ;

Stahl, Shannon S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863

← 1 2 3 4 5 6 →