A novel imidazol-2-ylidene as a ligand for palladium-catalyzed synthesis of oxyindoles from o-haloanilides

被引:51
作者
Zhang, TY [1 ]
Zhang, HB [1 ]
机构
[1] Lilly Corp Ctr, Lilly Res Labs, Chem Proc Res & Dev, Indianapolis, IN 46285 USA
关键词
catalysis; catalyst; oxindole; indole; palladium; imidazolylidene;
D O I
10.1016/S0040-4039(01)02138-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxyindoles were formed in good yields from 2-bromo- or chloroanilide in the presence of a base and a novel palladium imidazol-2-ylidene complex, through a process of metal-catalyzed intramolecular arylation of amide enolates. A wide range of substrates, including electron rich aryl chlorides, were found actives under the catalysis of this non-phosphinic, easily prepared ligand-metal system. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:193 / 195
页数:3
相关论文
共 52 条
[1]   Asymmetric arylation of ketone enolates [J].
Ahman, J ;
Wolfe, JP ;
Troutman, MV ;
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1918-1919
[2]  
Andreani A, 1976, Boll Chim Farm, V115, P741
[3]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[4]   NONTOXIC LIGANDS IN SAMARIUM DIIODIDE-MEDIATED CYCLIZATIONS [J].
CABRI, W ;
CANDIANI, I ;
COLOMBO, M ;
FRANZOI, L ;
BEDESCHI, A .
TETRAHEDRON LETTERS, 1995, 36 (06) :949-952
[5]   TANDEM WOLFF REARRANGEMENT TERT-AMINO-EFFECT SEQUENCE - SYNTHESIS OF 2-OXOINDOLLINIUM ENOLATE AND 1H-2-BENZOPYRANE DERIVATIVES [J].
CHANTEGREL, B ;
DESHAYES, C ;
FAURE, R .
TETRAHEDRON LETTERS, 1995, 36 (43) :7859-7862
[6]   A NOVEL ELECTROPHILIC N-AMIDATION VIA ELECTRON DEFICIENT COMPLEXES - ACTION OF FERRIC-CHLORIDE ON N-ACETYLOXYAMIDES [J].
CHEREST, M ;
LUSINCHI, X .
TETRAHEDRON LETTERS, 1989, 30 (06) :715-718
[7]   Manganese(III) reactions in N-heterocycle synthesis:: The preparation of substituted pyrrolidinones [J].
Davies, DT ;
Kapur, N ;
Parsons, AF .
TETRAHEDRON LETTERS, 1998, 39 (24) :4397-4400
[8]  
FERRIS P, 2000, CURR OPIN CENT PERIP, V2, P58
[9]   A NEW OXINDOLE SYNTHESIS [J].
FLEMING, I ;
MOSES, RC ;
TERCEL, M ;
ZIV, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :617-626
[10]  
FLEMING I, 1986, STUDIES ORGANIC CHEM, V26, P83