An improved 1,3-diene synthesis from alkyne and ethylene using cross-enyne metathesis

被引:81
作者
Tonogaki, K [1 ]
Mori, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1016/S0040-4039(02)00215-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of 1,3-diene from alkyne and ethylene (I atm) was improved using ruthenium carbene complex lb having heterocyclic carbene as a ligand. In this reaction, the heteroatom at the propargylic position was not required, although the reaction of alkyne with the first-generation ruthenium carbene complex la was affected by the substituent at the propargylic position. Various 1,3-dienes could be synthesized from alkynes and ethylene. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:2235 / 2238
页数:4
相关论文
共 50 条
[41]   THE SYNTHESIS OF ZIRCONOCENE-1,3-DIENE COMPLEXES USING VINYL ZIRCONIUM DERIVATIVES [J].
BECKHAUS, R ;
THIELE, KH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 268 (01) :C7-C8
[42]   SYNTHESIS OF 1,3-DIENE SILICON HYDROCARBONS AND THEIR CARBOFUNCTIONAL SUBSTITUTES BY WITTIG REACTION [J].
BELYAEV, NN ;
STADNICH.MD .
ZHURNAL OBSHCHEI KHIMII, 1971, 41 (08) :1877-&
[43]   ELECTROCHEMICAL SYNTHESIS OF 1,1-DICHLORO-4-METHYLPENTA-1,3-DIENE [J].
FECHTEL, U ;
MATSCHINER, H .
JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (04) :545-551
[44]   ORGN 421-New variations of the Trost-Lu alkyne to 1,3-diene isomerization reaction [J].
Yang, Daisy Die ;
Fu, Michael Yunyi ;
Kwong, Cathy Kar-Wing ;
Toy, Patrick H. .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
[45]   Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective Cycloisomerization Using Palladium-Catalyzed Alkyne-Alkyne Coupling [J].
Trost, Barry M. ;
Masters, James T. ;
Le Valliant, Franck ;
Lumb, Jean-Philip .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (20) :10023-10028
[46]   Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions [J].
Li, Wei ;
Schneider, Christopher M. ;
Georg, Gunda I. .
ORGANIC LETTERS, 2015, 17 (15) :3902-3905
[47]   ORGANOPLATINUM COMPLEXES RELATED TO CYCLODIMERIZATION OF 1,3-DIENES - REACTIONS OF 2,3-DIMETHYLBUTA-1,3-DIENE AND BUTA-1,3-DIENE WITH BIS(CYCLOOCTA-1,5-DIENE)PLATINUM OR BIS(ETHYLENE)TRIMETHYLPHOSPHINEPLATINUM [J].
BARKER, GK ;
GREEN, M ;
HOWARD, JAK ;
SPENCER, JL ;
STONE, FGA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3373-3374
[48]   FORMATION OF HETEROCYCLIC-COMPOUNDS FROM 1,3-DIAZABUTA-1,3-DIENE DERIVATIVES [J].
MATSUDA, I ;
YAMAMOTO, S ;
ISHII, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (14) :1528-1532
[49]   Nickel-catalyzed reductive 1,3-diene formation from the cross-coupling of vinyl bromides [J].
Sha, Yunfei ;
Liu, Jiandong ;
Wang, Liang ;
Liang, Demin ;
Wu, Da ;
Gong, Hegui .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) :4887-4890
[50]   SUBSTITUENT EFFECTS ON FORMATION AND BOND PROPERTIES OF TRICARBONYL(BUTA-1,3-DIENE)IRON, TRICARBONYL(TRANS-1-CHLOROBUTA-1,3-DIENE)IRON AND EXPERIMENTS ON SYNTHESIS OF TRICARBONYL(TRANS,TRANS 1,2,3,4-TETRACHLOROBUTA-1,3-DIENE)IRON [J].
BRUNE, HA ;
SCHWAB, W ;
HORLBECK, G .
TETRAHEDRON, 1972, 28 (16) :4455-&