Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes

被引：278

作者：

Ackermann, Lutz ^{[1
]}

Althammer, Andreas ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 10期

关键词：

C-C coupling; C-H activation; domino reactions; heterocycles; palladium;

D O I：

10.1002/anie.200603833

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) One after the other: A novel palladium-catalyzed domino reaction consisting of an amination and a direct C-H bond arylation allows for a general synthesis of annulated heterocycles starting from readily available 1,2-dichloroarenes and primary as well as secondary anilines (see scheme; Cy = cyclohexyl). This is high-lighted by an efficient synthesis of the natural product murrayafoline A. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1627 / 1629

页数：3

共 35 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] 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
[3] General and efficient indole syntheses based on catalytic amination reactions
Ackermann, L
[J]. ORGANIC LETTERS, 2005, 7 (03) : 439 - 442
[4] [Anonymous], 2006, ANGEW CHEM
[5] [Anonymous], HDB C H TRANSFORMATI
[6] [Anonymous], 2002, J ORGANOMET CHEM
[7] A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation
Bedford, RB
Cazin, CSJ
[J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2310 - 2311
[8] Beller M., 2004, Transition Metals for Organic Synthesis, DOI 10.1002/9783527619405
[9] A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction
Bressy, C
Alberico, D
Lautens, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13148 - 13149
[10] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
Campeau, LC
Parisien, M
Jean, A
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590

← 1 2 3 4 →