64207-12-1

Upstream product

• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 142-29-0 cyclopentene 
• 96-09-3 styrene oxide 
• 36291-48-2 3-bromocyclopentene 
• 196876-95-6 cyclopent-2-enylphenylmethanol 
• 100-52-7 benzaldehyde 
• 33524-58-2 cyclopent-3-en-1-yl(phenyl)methanone 
• 3462-52-0 1-phenyl-2-(2-propen-1-yl)-4-penten-1-one 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 100702-21-4 2-<(2-cyclopentenyl)oxy>-1-phenylethanol 
• 65755-85-3 (2-cyclopentenyloxy)acetophenone 
• 65755-96-6 2-(2-cyclopentenyl)-2-phenyl-2-(trimethylsiloxy)acetaldehyde 

Relevant academic research and scientific papers

Palladium-Catalyzed Allylic Alkylation of 2-Aryl-1,3-Dithianes, an Umpolung Synthesis of β,γ-Unsaturated Ketones

Palladium-catalyzed allylic alkylation of 2-aryl-1,3-dithianes at room temperature is described. A variety of cyclic and acyclic electrophiles successfully coupled with in-situ generated 2-sodio-1,3-dithiane nucleophiles to afford the allylated products in good to excellent yields (25 examples). Deprotection of these products leads to valuable β,γ-unsaturated ketones. Direct synthesis of such β,γ-unsaturated ketones via a one-pot allylation-oxidation protocol is also presented. Investigation into the stereochemistry of the allylation reaction revealed that the 2-sodio-1,3-dithiane nucleophile behaves as a “soft” nucleophile, which underwent external attack on the π-allyl palladium complex to provide retention of stereochemistry (double inversion pathway). Additionally, the utility of this method was demonstrated through a sequential one-pot allylation-Heck cyclization to produce asterogynin derivatives, which are important bioactive compounds in medicinal chemistry. (Figure presented.).

Iminoxyl radical-promoted dichotomous cyclizations: Efficient oxyoximation and aminooximation of alkenes

A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from β,γ- and γ,δ-unsaturated ketoximes, respectively.

Ruthenium nitronate complexes as tunable catalysts for olefin metathesis and other transformations

Novel ruthenium(ii) complexes were obtained as a result of a stoichiometric reaction of Grubbs' benzylidene second generation catalysts with 3-nitropropene. These stable complexes, formally ruthenaisoxazole N-oxide derivatives, display activity in both me

Oxime radical promoted dioxygenation, oxyamination, and diamination of alkenes: Synthesis of isoxazolines and cyclic nitrones

Up the tempo: The intramolecular addition of oxime radicals to C=C bonds was achieved by using DEAD and TEMPO to give 4,5-dihydroisoxazoles as a result of a C=O bond-forming, 5-exo-trig cyclization. γ,δ-Unsaturated ketoximes also reacted to afford cyclic nitrones through C-N bond formation. The reactions offer a metal-free approach for the vicinal difunctionalization of unactivated alkenes. Copyright

Palladium-Catalyzed Cross-Carbonylation of Aryl Iodides with Five-Membered Cyclic Olefins

Intermolecular cross-carbonylation of aryl iodides with five-membered cyclic olefins such as dihydrofurans and cyclopentene was found to proceed by using a catalyst system of PdCl2/PPh3 under CO (3-5 atm) in the presence of a tertiary amine.With 2,3- and 2,5-dihydrofurans, 2-aroyl-4,5-dihydro- and 3-aroyl-2,3-dihydrofurans were obtained as the predominant products, respectively, while the reaction of iodobenzene with cyclopentene gave a mixture of three regioisomers of benzoylcyclopentene.The yields of the products were observed to be markedly influenced by the amount of triphenylphosphine added.

Regiospecific Synthesis of β, γ-Unsaturated Ketones from Allylic Alcohols. Claisen Rearrangement of α-Allyloxy Ketone Enol Derivatives

β,γ-Unsaturated ketones are prepared with regiospecific C-C bond formation at the former γ-position of primary, secondary, or tertiary allylic alcohol precursors by a process involving sigmatropic Claisen rearrangement of intermediate α-allyloxy ket