Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoalkynes:: a new and efficient catalyst for cyclotrimerization of alkynes

被引:73
作者
Takeuchi, R
Tanaka, S
Nakaya, Y
机构
[1] Yokohama City Univ, Fac Sci, Dept Environm Sci, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan
[2] Yokohama City Univ, Grad Sch Integrated Sci, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan
关键词
iridium and compounds; diynes; cycloadditions; metallacycles; alkynes;
D O I
10.1016/S0040-4039(01)00338-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[Ir(cod)Cl](2) combined with dppe was found to be a new and efficient catalyst for [2+2+2] cycloaddition. Dimethyl dipropargylmalonate reacted with 1-hexyne in the presence of a catalytic amount of [Ir(cod)C1](2) combined with dppe at room temperature in 20 min to give an indane derivative in 84% yield. Various functionalized monoalkynes can be used for this [2+2+2] cycloaddition. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2991 / 2994
页数:4
相关论文
共 25 条
[1]   METALOCYCLOPENTADIENE COMPLEXES OF IRIDIUM AND RHODIUM AND THEIR ROLE IN CATALYTIC CYCLOTRIMERIZATION OF DISUBSTITUTED ACETYLENES [J].
COLLMAN, JP ;
KANG, JW ;
LITTLE, WF ;
SULLIVAN, MF .
INORGANIC CHEMISTRY, 1968, 7 (07) :1298-&
[2]   The first metallacyclopentadiene(alkyne) complexes and their discrete isomerization to η4-bound arenes:: The missing link in the prevalent mechanism of transition metal catalyzed alkyne cyclotrimerizations, as exemplified by cyclopentadienylcobalt [J].
Diercks, R ;
Eaton, BE ;
Gürtzgen, S ;
Jalisatgi, S ;
Matzger, AJ ;
Radde, RH ;
Vollhardt, KPC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8247-8248
[3]   Co-cyclizations of nitrogen-containing acetylenes induced by a nickel triphenylphosphine complex to give aminoindane, isoindoline and isoindolinone derivatives [J].
Duckworth, DM ;
LeeWong, S ;
Slawin, AMZ ;
Smith, EH ;
Williams, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (08) :815-821
[4]   RHODIUM-CATALYZED [2+2+2]-CYCLOADDITIONS OF ACETYLENES [J].
GRIGG, R ;
SCOTT, R ;
STEVENSON, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1357-1364
[5]  
Grotjahn D. B, 1995, COMPREHENSIVE ORGANO, V12, P741
[6]   CATALYTIC HEAD-TO-HEAD ALKYNE DIMERIZATION TO GIVE Z-ENYNES [J].
JUN, CH ;
LU, Z ;
CRABTREE, RH .
TETRAHEDRON LETTERS, 1992, 33 (47) :7119-7120
[7]   Transition metal-mediated cycloaddition reactions [J].
Lautens, M ;
Klute, W ;
Tam, W .
CHEMICAL REVIEWS, 1996, 96 (01) :49-92
[8]   Anti-Markovnikov olefin arylation catalyzed by an iridium complex [J].
Matsumoto, T ;
Taube, DJ ;
Periana, RA ;
Taube, H ;
Yoshida, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (30) :7414-7415
[9]   PARALLEL REACTION PATHWAYS IN COBALT-CATALYZED CYCLOTRIMERIZATION OF ACETYLENES [J].
MCALISTER, DR ;
BERCAW, JE ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1666-1668
[10]   RHODIUM-CATALYZED ALKYNE CYCLOTRIMERIZATION STRATEGIES FOR C-ARYLGLYCOSIDE SYNTHESIS [J].
MCDONALD, FE ;
ZHU, HYH ;
HOLMQUIST, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (24) :6605-6606