Chemistry of aminophenols. Part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles

被引：80

作者：

Dai, WM ^{[1
]}

Guo, DS

Sun, LP

机构：

[1] Hong Kong Univ Sci & Technol, Biotechnol Res Inst, Combinatorial Chem Lab, Kowloon, Hong Kong, Peoples R China

[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 31期

关键词：

coupling reactions; indoles; phenols; triflates;

D O I：

10.1016/S0040-4039(01)00965-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and general synthesis of indoles has been established by utilizing 2-aminophenols as the starting materials. The key step is a modified Pd(0)-Cu(I)-catalyzed cross-coupling of 1-alkynes with 2-carboxamidoaryl triflates in the presence of n-Bu4NI as the additive. The 2-alkynylanilides obtained were subjected to an alkoxide-mediated cyclization to provide a number of indole containing compounds possessing substituents at the C2, C4, C5, and/or C6 position(s) in good overall yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5275 / 5278

页数：4

相关论文

共 65 条

[1] AN EFFICIENT PALLADIUM-CATALYZED REACTION OF VINYL AND ARYL HALIDES OR TRIFLATES WITH TERMINAL ALKYNES [J].

ALAMI, M ;

FERRI, F ;

LINSTRUMELLE, G .

TETRAHEDRON LETTERS, 1993, 34 (40) :6403-6406

[2] INTIMATE MECHANISM OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES IN THE PRESENCE OF HALIDE-IONS AND ITS RELEVANCE TO THE MECHANISM OF PALLADIUM-CATALYZED NUCLEOPHILIC SUBSTITUTIONS [J].

AMATORE, C ;

JUTAND, A ;

SUAREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9531-9541

[3] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].

AMATORE, C ;

AZZABI, M ;

JUTAND, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8375-8384

[4]

ARCADI A, 1992, TETRAHEDRON LETT, V33, P3915

[5] 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

[6] 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

[7] INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES [J].

CASTRO, CE ;

GAUGHAN, EJ ;

OWSLEY, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4071-+

[8] SYNTHESIS OF THE 5-HT1D RECEPTOR AGONIST MK-0462 VIA A PD-CATALYZED COUPLING REACTION [J].

CHEN, CY ;

LIEBERMAN, DR ;

LARSEN, RD ;

REAMER, RA ;

VERHOEVEN, TR ;

REIDER, PJ ;

COTTRELL, IF ;

HOUGHTON, PG .

TETRAHEDRON LETTERS, 1994, 35 (38) :6981-6984

[9] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones [J].

Chen, CY ;

Lieberman, DR ;

Larsen, RD ;

Verhoeven, TR ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2676-2677

[10] PALLADIUM-CATALYZED REACTION OF PHENYL FLUOROALKANESULFONATES WITH ALKYNES AND ALKENES [J].

CHEN, QY ;

YANG, ZY .

TETRAHEDRON LETTERS, 1986, 27 (10) :1171-1174

← 1 2 3 4 5 6 7 →