Highly regioselective palladium-catalyzed condensation of terminal acetylenes with 2,5-diiodobenzoic acid

被引:13
作者
Balavoine, F
Madec, D
Mioskowski, C [1 ]
机构
[1] CEA Saclay, Serv Mol Marquees, DSV, DSM, F-91191 Gif Sur Yvette, France
[2] Univ Strasbourg 1, CNRS, Lab Synth Bioorgan, F-67401 Illkirch, France
关键词
alkynes; aryl halides; Sonogashira reaction; regioselection;
D O I
10.1016/S0040-4039(99)01697-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-catalyzed coupling reactions between terminal alkynes and 2,5-diiodobenzoic acid have been shown to be highly regioselective, giving a rapid and efficient route for the synthesis of disymmetric 2,5-bis ethynyl benzoic acid derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8351 / 8354
页数:4
相关论文
共 7 条
[1]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[2]   5,6,11,12,17,18-hexadehydro-1,4,7,10,13,16-hexaethynyltribenzo[a,e,i]cyclododecene: Synthesis and CpCo-catalyzed cycloisomerization to the first superdelocalized oligophenylenes [J].
Eickmeier, C ;
Junga, H ;
Matzger, AJ ;
Scherhag, F ;
Shim, M ;
Vollhardt, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (19) :2103-2108
[3]   Palladium-catalysed heteroannulation with terminal alkynes: synthesis of phthalides [J].
Kundu, NG ;
Pal, M ;
Nandi, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :561-568
[4]   SYNTHESIS OF ISOCOUMARINS FROM O-IODOBENZOIC ACID AND TERMINAL ACETYLENES MEDIATED BY PALLADIUM COMPLEXES AND ZINC-CHLORIDE [J].
LIAO, HY ;
CHENG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3711-3716
[5]   SELECTIVE PALLADIUM-CATALYZED VINYLIC SUBSTITUTIONS WITH BROMOIODO AROMATICS [J].
PLEVYAK, JE ;
DICKERSON, JE ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (23) :4078-4080
[6]  
SONOGASHIRA K, 1990, COMPREHENSIVE ORGANI, V3, P545
[7]   PALLADIUM-CATALYZED ALKENYLATION AND ALKYNYLATION OF POLYHALOARENES [J].
TAO, WJ ;
NESBITT, S ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :63-69