Palladium-Catalyzed Direct C-3 Arylations of Indoles with an Air-Stable HASPO

被引:79
作者
Ackermann, Lutz [1 ]
Barfuesser, Sebastian [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
关键词
C-H bond functionalization; heteroarenes; indoles; regioselectivity; palladium; H BOND ACTIVATION; CROSS-COUPLING REACTIONS; C-H; FREE (NH)-INDOLES; PHOSPHINE OXIDES; ROOM-TEMPERATURE; ARYL; FUNCTIONALIZATION; PRELIGANDS; CHLORIDES;
D O I
10.1055/s-0028-1087951
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient direct arylations of indoles occurred highly regioselectively at position C-3 with an in situ generated palladium complex derived from an air-stable HASPO, which enabled syntheses of diversely functionalized indoles, also with sterically hindered substrates.
引用
收藏
页码:808 / 812
页数:5
相关论文
共 48 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]   Cross-coupling reactions of aryl and vinyl chlorides catalyzed by a palladium complex derived from an air-stable H-phosphonate [J].
Ackermann, L ;
Gschrei, CJ ;
Althammer, A ;
Riederer, M .
CHEMICAL COMMUNICATIONS, 2006, (13) :1419-1421
[3]   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
[4]   Modular diamino- and dioxophosphine oxides and chlorides as ligands for transition-metal-catalyzed C-C and C-N couplings with aryl chlorides [J].
Ackermann, L ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2444-2447
[5]   General and efficient indole syntheses based on catalytic amination reactions [J].
Ackermann, L .
ORGANIC LETTERS, 2005, 7 (03) :439-442
[6]   Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline [J].
Ackermann, L ;
Kaspar, LT ;
Gschrei, CJ .
CHEMICAL COMMUNICATIONS, 2004, (24) :2824-2825
[7]  
ACKERMANN L, 2009, MODERN ARYLATION REA
[8]   Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations [J].
Ackermann, Lutz ;
Mulzer, Michael .
ORGANIC LETTERS, 2008, 10 (21) :5043-5045
[9]   Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Althammer, Andreas .
ORGANIC LETTERS, 2008, 10 (11) :2299-2302
[10]   Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Born, Robert .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) :741-748