One-Pot/Four-Step/Palladium-Catalyzed Synthesis of Indole Derivatives: The Combination of Heterogeneous and Homogeneous Systems

被引：45

作者：

Sakai, Hayato ^{[1
]}

Tsutsumi, Ken ^{[1
]}

Morimoto, Tsumoru ^{[1
]}

Kakiuchi, Kiyomi ^{[1
]}

机构：

[1] NAIST, Grad Sch Mat Sci, Nara 6300192, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

homogeneous catalysis; indoles; one-pot multi-step synthesis; palladium; supported catalysts;

D O I：

10.1002/adsc.200800405

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

One-pot, four-step syntheses of indoles using both solid-supported heterogeneous and homogeneous palladium catalysts and reagents were carried out. Such a combination of these two-phase catalysts and reagents causes a dramatic increase in yield, and it is a simple process. The presented methodology is effective for four-step reactions to provide various functionalized indoles.

引用

收藏

页码：2498 / 2502

页数：5

相关论文

共 34 条

[1] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES [J].

ARCADI, A ;

CACCHI, S ;

MARINELLI, F .

TETRAHEDRON LETTERS, 1989, 30 (19) :2581-2584

[2] Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines [J].

Bahekar, Rajesh H. ;

Jain, Mukul R. ;

Goel, Ashish ;

Patel, Dipam N. ;

Prajapati, Vijay M. ;

Gupta, Arun A. ;

Patel, Pankaj R. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (09) :3248-3265

[3] Synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols [J].

Botta, M ;

Summa, V ;

Corelli, F ;

DiPietro, G ;

Lombardi, P .

TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1263-1266

[4] Investigating PdEnCat catalysis [J].

Broadwater, SJ ;

McQuade, DT .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05) :2131-2134

[5] One-pot multi-step synthesis: a challenge spawning innovation [J].

Broadwater, SJ ;

Roth, SL ;

Price, KE ;

Kobaslija, M ;

McQuade, DT .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (16) :2899-2906

[6] Concepts of nature in organic synthesis: Cascade catalysis and multistep conversions in concert [J].

Bruggink, A ;

Schoevaart, R ;

Kieboom, T .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (05) :622-640

[7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[8] Silica-supported phosphine palladium(0) complex catalyzed phenylation of acid chlorides and aryl iodides by sodium tetraphenylborate [J].

Cai, MZ ;

Song, CS ;

Huang, X .

SYNTHETIC COMMUNICATIONS, 1998, 28 (04) :693-700

[9] New hetero-bimetallic Pd-Cu catalysts for the one-pot indole synthesis via the Sonogashira reaction [J].

Chouzier, S ;

Gruber, M ;

Djakovitch, L .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 212 (1-2) :43-52

[10] Heterogeneous palladium catalysts applied to the synthesis of 2- and 2,3-functionalised indoles [J].

Djakovitch, L ;

Dufaud, V ;

Zaidi, R .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (06) :715-724

← 1 2 3 4 →