N-Alkoxyimidazolylidene Transition-Metal Complexes:  Application to [5+2] and [4+2] Cycloaddition Reactions

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....

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Bibliographic Details
Published inOrganometallics Vol. 26; no. 18; pp. 4541 - 4545
Main Authors Gómez, Fernando J, Kamber, Nahrain E, Deschamps, Nicole M, Cole, Adam P, Wender, Paul A, Waymouth, Robert M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.08.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC CATALYSIS
RHODIUM
PALLADIUM COMPLEXES
HETEROCYCLIC CARBENE COMPLEXES
DIELS-ALDER REACTION
NHC LIGANDS
STRUCTURAL-CHARACTERIZATION
VINYLCYCLOPROPANES
STEREODIRECTING LIGANDS
CYCLOISOMERIZATION REACTIONS
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Summary: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.
Bibliography:ark:/67375/TPS-DSQHWJ1C-7
istex:81C16E6690FB2E4CC1FF289E5EFABC04D511AC51
ISSN:0276-7333
1520-6041
DOI:10.1021/om700493y