SDS of cas: 92390-26-6. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium, is researched, Molecular C18H28ClRu, CAS is 92390-26-6, about Selective ruthenium-catalyzed transformations of enynes with diazoalkanes into alkenylbicyclo[3.1.0]hexanes. Author is Monnier, Florian; Vovard-Le Bray, Chloe; Castillo, Dante; Aubert, Vincent; Derien, Sylvie; Dixneuf, Pierre H.; Toupet, Loic; Ienco, Andrea; Mealli, Carlo.
Reaction of a variety of CCH bond-containing 1,6-enynes, e.g. the N-propargylbutenamine I, with N2CHSiMe3 in the presence of RuCl(COD)Cp* as catalyst precursor leads, at room temperature, to the general formation of alkenylbicyclo[3.1.0]hexanes, e.g. the (trimethylsilylvinyl)azabicyclohexane II, with high Z-stereoselectivity of the alkenyl group and cis arrangement of the alkenyl group and an initial double-bond substituent, for an E-configuration of this double bond. The stereochem. is established by determining the X-ray structures of three bicyclic products. The same reaction with 1,6-enynes bearing an R substituent on the C1 carbon of the triple bond results in either cyclopropanation of the double bond with bulky R groups (SiMe3, Ph) or formation of alkylidene-alkenyl five-membered heterocycles, e.g. the ethylidenepyrrolidine III, resulting from a β-elimination process with less bulky R groups, e.g. Me or CH2CH:CH2. The reaction can be applied to in situ desilylation in methanol and direct formation of vinylbicyclo[3.1.0]hexanes and to the formation of some alkenylbicyclo[4.1.0]heptanes from 1,7-enynes. The catalytic formation of alkenylbicyclo[3.1.0]hexanes also takes place with enynes and N2CHCO2Et or N2CHPh. The reaction can be understood to proceed by an initial [2+2] addition of the Ru:CHSiMe3 bond with the enyne CCH bond, successively leading to an alkenylruthenium-carbene and a key alkenyl bicyclic ruthenacyclobutane, which promotes the cyclopropanation, rather than metathesis, into bicyclo[3.1.0]hexanes. D. functional theory calculations performed starting from the model system Ru(HCCH)(CH2:CH2)Cl(C5H5) show that the transformation into a ruthenacyclobutane intermediate occurs with a temporary η3-coordination of the cyclopentadienyl ligand. This step is followed by coordination of the alkenyl group, which leads to a mixed alkyl-allyl ligand. Because of the non-equivalence of the terminal allylic carbon atoms, their coupling favors cyclopropanation rather than the expected metathesis process. A direct comparison of the energy profiles with respect to those involving the Grubbs catalyst is presented, showing that cyclopropanation is favored with respect to enyne metathesis.
《Selective ruthenium-catalyzed transformations of enynes with diazoalkanes into alkenylbicyclo[3.1.0]hexanes》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(Chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium)SDS of cas: 92390-26-6.
Reference:
Chapter 1 An introduction to palladium catalysis,
Palladium/carbon catalyst regeneration and mechanical application method