N-Alkoxyimidazolylidene transition-metal complexes:: Application to [5+2] and [4+2] cycloaddition reactions

被引:38
作者
Gomez, Fernando J. [1 ]
Kamber, Nahrain E. [1 ]
Deschamps, Nicole M. [1 ]
Cole, Adam P. [1 ]
Wender, Paul A. [1 ]
Waymouth, Robert M. [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/om700493y
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Silver(I) bis[(benzyloxy)imidazol-2-ylidene] complex 6 is prepared by reaction of an alkoxyimidazolium bromide (4) with Ag2O. In situ deprotonation of the alkoxyimidazolium bromide 4 afforded the rhodium(I) and palladium(II) complexes 7 and 8, whose structures were verified by X-ray crystallography. Rhodium(I) ( benzyloxy) imidazolylidene complex 7 efficiently catalyzes the [5+2] cycloaddition reaction of an yne-vinylcyclopropane (93%) and the [4+2] cycloaddition reaction of a diene-yne (99%) at room temperature in minutes.
引用
收藏
页码:4541 / 4545
页数:5
相关论文
共 50 条
[21]   TRANSITION-METAL MEDIATED [4+2] CYCLOADDITION OF 1,3-DIENES WITH ALKYNES IN THE GAS-PHASE [J].
BAKHTIAR, R ;
DRADER, JJ ;
LARSON, J ;
JACOBSON, DB .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 :384-INOR
[22]   NOVEL CYCLOADDITION REACTIONS OF ISOCYANIDES WITH DIPHENYLACETYLENE USING TRANSITION-METAL COMPLEXES [J].
SUZUKI, Y ;
TAKIZAWA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (14) :837-&
[23]   Metal-mediated cycloaddition reactions of the eta(5)-cyclohexadienyl ligand. Synthesis and reactions of [5+2] single and [5+2],homo[5+2] double cyclohexadienyl-alkyne adducts of manganese [J].
Hung, HJ ;
Sheridan, JB ;
Cote, ML ;
Lalancette, RA .
ORGANOMETALLICS, 1996, 15 (21) :4575-4585
[24]   STUDIES ON THE REACTIONS OF TRANSITION-METAL HYDRIDES WITH TRANSITION-METAL DINITROGEN COMPLEX (MO(N2)2(DPPE)2) AND (C6H5N2)BF4 [J].
BEI, M ;
WANG, S ;
WANG, J ;
WU, Y ;
CAO, S ;
GUO, H .
KEXUE TONGBAO, 1982, 27 (02) :177-178
[25]   REACTIONS OF COMPLEX LIGANDS .25. [4+2]CYCLOADDITION TO ALKINYLCARBENE COMPLEXES [J].
DOTZ, KH ;
KUHN, W .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 286 (02) :C23-C26
[26]   Intramolecular [4+2]-cycloaddition reactions of cyclic 2-thiomethyl-5-amidofurans [J].
Ginn, JD ;
Lynch, SM ;
Padwa, A .
TETRAHEDRON LETTERS, 2000, 41 (49) :9387-9391
[27]   [4+2] CYCLOADDITION REACTIONS OF N-SULFINYLCARBOXAMIDES .2. REACTIONS WITH UNSYMMETRICALLY SUBSTITUTED ALKENES [J].
CARPANELLI, C ;
GAIANI, G ;
SANCASSAN, F .
GAZZETTA CHIMICA ITALIANA, 1984, 114 (9-10) :399-403
[28]   PHOTOCHEMICAL-REACTIONS OF TRANSITION-METAL ORGANYL COMPLEXES WITH OLEFINS .10. LIGHT-INDUCED FORMAL [5+2] CYCLOADDITIONS AT MANGANESE [J].
KREITER, CG ;
KOCH, EC ;
FRANK, W ;
REISS, G .
INORGANICA CHIMICA ACTA, 1994, 220 (1-2) :77-83
[29]   Rhodium-catalyzed [5+2] cycloaddition reactions in water [J].
Wender, PA ;
Love, JA ;
Williams, TJ .
SYNLETT, 2003, (09) :1295-1298
[30]   [5+2] Cycloaddition Reactions in Organic and Natural Product Synthesis [J].
Ylijoki, Kai E. O. ;
Stryker, Jeffrey M. .
CHEMICAL REVIEWS, 2013, 113 (03) :2244-2266