Ruthenium-carbene catalysts for the synthesis of 2,3-dimethylfuran

被引:92
作者
Cetinkaya, B [1 ]
Ozdemir, I [1 ]
Bruneau, C [1 ]
Dixneuf, PH [1 ]
机构
[1] UNIV RENNES 1,CHIM COORDINAT ORGAN LAB,URA CNRS 415,F-35042 RENNES,FRANCE
关键词
ruthenium-carbene catalysts; activation of Z-enynols; catalytic synthesis of 2,3-dimethylfuran;
D O I
10.1016/S1381-1169(96)00239-7
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A variety of neutral arene-ruthenium-carbenes of type (arene)RuCl2(=C(NR)CH(2)CH(2)NR) have been used for the catalytic transformation of (Z)-3-methylpent-2-en-4-yn-l-ol into 2,3-dimethylfuran. The catalytic reaction takes place at 80 degrees C with mononuclear complexes III-V to afford the furan in similar to 90% yield. The binuclear catalysts VIa and VIIa having a linked bis-carbene bridge operate at room temperature to initiate an exothermic reaction offering 90-97% of furan.
引用
收藏
页码:L1 / L4
页数:4
相关论文
共 36 条
[1]   ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].
BENNETT, MA ;
SMITH, AK .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241
[2]   (ETA-6-HEXAMETHYLBENZENE)RUTHENIUM COMPLEXES [J].
BENNETT, MA ;
HUANG, TN ;
MATHESON, TW ;
SMITH, AK .
INORGANIC SYNTHESES, 1982, 21 :74-78
[3]   A RU(II) ENYNYL COMPLEX MEDIATES THE CATALYTIC DIMERIZATION OF 1-ALKYNES TO Z-1,4-DISUBSTITUTED ENYNES [J].
BIANCHINI, C ;
PERUZZINI, M ;
ZANOBINI, F ;
FREDIANI, P ;
ALBINATI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5453-5454
[4]   CATALYTIC INCORPORATION OF CO-2 INTO ORGANIC SUBSTRATES - SYNTHESIS OF UNSATURATED CARBAMATES, CARBONATES AND UREAS [J].
BRUNEAU, C ;
DIXNEUF, PH .
JOURNAL OF MOLECULAR CATALYSIS, 1992, 74 (1-3) :97-107
[5]   RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS [J].
BRUNEAU, C ;
NEVEUX, M ;
KABOUCHE, Z ;
RUPPIN, C ;
DIXNEUF, PH .
SYNLETT, 1991, (11) :755-763
[6]  
BRUNEAU C, 1994, INORG CHIM ACTA, V222, P154
[7]  
BRUNEAU C, 1995, ALLENES CUMULENES CO, V1, P953
[8]  
CETINKAYA B, IN PRESS
[9]   CONCOMITANT CATALYTIC TRANSFORMATIONS OF GEMINAL ETHYNYL AND HYDROXY-GROUPS OF STEROIDS INTO ACETYL AND ESTER FUNCTIONS WITH RETENTION OF CONFIGURATION BY [RU(MU-O2CH)(CO)(2)(PPH(3))](2) [J].
DARCEL, C ;
BRUNEAU, C ;
DIXNEUF, PH ;
NEEF, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :333-334
[10]   Ruthenium-catalysed coupling of allyl alcohol with alkynes: A new route to gamma delta-unsaturated acetals and aldehydes [J].
Derien, S ;
Jan, D ;
Dixneuf, PH .
TETRAHEDRON, 1996, 52 (15) :5511-5524