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

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates
Ackermann, L
Althammer, A
Born, R
[J]. 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
Ackermann, L
Gschrei, CJ
Althammer, A
Riederer, M
[J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1419 - 1421
[3] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides
Ackermann, L
Born, R
Spatz, JH
Meyer, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) : 7216 - 7219
[4] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides
Ackermann, L
[J]. ORGANIC LETTERS, 2005, 7 (14) : 3123 - 3125
[5] Modular diamino- and dioxophosphine oxides and chlorides as ligands for transition-metal-catalyzed C-C and C-N couplings with aryl chlorides
Ackermann, L
Born, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) : 2444 - 2447
[6] General and efficient indole syntheses based on catalytic amination reactions
Ackermann, L
[J]. ORGANIC LETTERS, 2005, 7 (03) : 439 - 442
[7] TiCl4/t-BuNH2 as the sole catalyst for a hydroamination-based Fischer indole synthesis
Ackermann, L
Born, R
[J]. TETRAHEDRON LETTERS, 2004, 45 (52) : 9541 - 9544
[8] Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline
Ackermann, L
Kaspar, LT
Gschrei, CJ
[J]. CHEMICAL COMMUNICATIONS, 2004, (24) : 2824 - 2825
[9] TiCl4-catalyzed intermolecular hydroamination reactions of norbornene
Ackermann, L
Kaspar, LT
Gschrei, CJ
[J]. ORGANIC LETTERS, 2004, 6 (15) : 2515 - 2518
[10] TiCl4-catalyzed intermolecular hydroamination reactions
Ackermann, L
[J]. ORGANOMETALLICS, 2003, 22 (22) : 4367 - 4368

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