One-pot 2-aryl/vinylindole synthesis consisting of a ruthenium-catalyzed hydroamination and a palladium-catalyzed Heck reaction using 2-chloroaniline

被引：37

作者：

Ackermann, Lutz ^{[1
]}

Althammer, Andreas ^{[1
]}

机构：

[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany

来源：

SYNLETT | 2006年 / 18期

关键词：

aryl chlorides; Heck reaction; hydroamination; palladium; ruthenium;

D O I：

10.1055/s-2006-950440

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot synthesis of 2-aryl- and 2-vinytindoles based on a ruthenium-catalyzed hydroamination and a palladium-catalyzed intramolecular Heck reaction is reported. The ruthenium-catalyzed addition reaction was applied to terminal as well as internal alkynes. Intramolecular Heck reactions of the resulting 2-chloroanilino enamines were achieved using an in situ generated palladium complex derived from an N-heterocyclic carbene.

引用

页码：3125 / 3129

页数：5

共 46 条

[21] PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES
HECK, RF
NOLLEY, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) : 2320 - &
[22] Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
[23] 2-Y
[24] Titanium-catalyzed intermolecular hydroamination of vinylarenes
Kaspar, LT
Fingerhut, B
Ackermann, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (37) : 5972 - 5974
[25] New mechanism for the intermolecular hydroamination of alkynes: Catalysis by dinuclear ruthenium complexes with a rigid dicyclopentadienyl ligand
Klein, DP
Ellern, A
Angelici, RJ
[J]. ORGANOMETALLICS, 2004, 23 (24) : 5662 - 5670
[26] A simple and efficient iron-catalyzed intramolecular hydroamination of unactivated olefins
Komeyama, Kimihiro
Morimoto, Takayuki
Takaki, Ken
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) : 2938 - 2941
[27] RUTHENIUM COMPLEX-CATALYZED ADDITION OF N-ARYL SUBSTITUTED AMIDES TO ALKYNES - NOVEL SYNTHESIS OF ENAMIDES
KONDO, T
TANAKA, A
KOTACHI, S
WATANABE, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (04) : 413 - 414
[28] Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes
Larock, RC
Yum, EK
Refvik, MD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7652 - 7662
[29] Palladium-catalyzed annulation
Larock, RC
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) : 111 - 124
[30] Link J. T, 2002, ORG REACTIONS, V60, P160

← 1 2 3 4 5 →