Intramolecular cyclization using palladium-catalyzed arylation toward formyl and nitro groups

被引:73
作者
Muratake, H
Nakai, H
机构
[1] Res Fdn Itsuu Lab, Setagaya Ku, Tokyo 1580094, Japan
[2] Shionogi & Co Ltd, Shionogi Res Labs, Fukushima Ku, Osaka 5530002, Japan
关键词
aldehydes; arylation; nitro compounds; palladium and compounds;
D O I
10.1016/S0040-4039(99)00185-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Intramolecular arylation of properly designed substrates bearing a formyl or nitro terminating group was achieved employing a PdCl2(Ph3P)(2)-Cs2CO3 catalyst system to form various carbocyclic compounds. Arylation toward the formyl group occurred at the a-position (alpha-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the substrates and on the reaction solvent. The cl-arylated secondary nitro group was partially transformed to ketone, whereas the tertiary nitro group was partially eliminated to a styrene type of olefin. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2355 / 2358
页数:4
相关论文
共 14 条
[1]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[2]   Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383
[3]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[4]  
HECK RF, 1982, ORG REACTIONS, V27, P345
[5]   Palladium-catalyzed coupling reaction of 4-alkylnitrobenzenes with aryl bromides at their benzylic position [J].
Inoh, J ;
Satoh, T ;
Pivsa-Art, S ;
Miura, M ;
Nomura, M .
TETRAHEDRON LETTERS, 1998, 39 (26) :4673-4676
[6]   THE ARYLATION OF NITROALKANES AND NITRONATE SALTS WITH ARYLLEAD TRIACETATES [J].
KOZYROD, RP ;
PINHEY, JT .
TETRAHEDRON LETTERS, 1981, 22 (08) :783-784
[7]   Palladium-catalyzed intramolecular alpha-arylation of aliphatic ketones [J].
Muratake, H ;
Natsume, M .
TETRAHEDRON LETTERS, 1997, 38 (43) :7581-7582
[8]   A novel phenol-forming reaction for preparation of benzene, furan, and thiophene analogs of CC-1065/duocarmycin pharmacophores [J].
Muratake, H ;
Hayakawa, A ;
Natsume, M .
TETRAHEDRON LETTERS, 1997, 38 (43) :7577-7580
[9]   Palladium-catalyzed alpha-arylation of ketones [J].
Palucki, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (45) :11108-11109
[10]   Palladium-catalyzed coupling reaction of salicylaldehydes with aryl iodides via cleavage of the aldehyde C-H bond [J].
Satoh, T ;
Itaya, T ;
Miura, M ;
Nomura, M .
CHEMISTRY LETTERS, 1996, (09) :823-824