85964-37-0

Upstream product

• 27200-79-9 p-bromophenylacetaldehyde 
• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 72863-20-8 α,α-Dimethylallyl phenyl sulfone 
• 106-40-1 4-bromo-aniline 
• 589-87-7 1,4-bromoiodobenzene 
• 870-63-3 prenyl bromide 
• 87077-84-7 4-(4-bromophenyl)-2-methyl-2-butanol 

Downstream Products

• 90433-29-7 4-(3-methylbut-2-en-1-yl)benzonitrile 
• 1193753-07-9 1-bromo-4-(2,3-epoxy-3-methylbuten-1-yl)benzene 

Relevant academic research and scientific papers

A General Photocatalytic Route to Prenylation

Prenylation is an essential reaction on which nature relies to modify properties of molecules and build terpenoids, but remains a challenging chemical reaction. Aiming to capitalize on recent advances in photocatalysis to easily and cleanly generate a broad range of carbon based radicals, we have developed a prenyl transfer reagent that is captured by transiently generated radicals. The reagent can be made in bulk, is bench stable, and broadly applicable such that it can be used with existing photocatalytic methods with very few changes to reaction conditions. Ultimately, this provides a true drop-in solution for prenylation, expanding the scope of substrates that can be readily prenylated.

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction

A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).

Metal-Free Dehydrogenative Diels-Alder Reactions of Prenyl Derivatives with Dienophiles via a Thermal Reversible Process

An efficient dehydrogenative Diels-Alder reaction of prenyl derivatives with dienophiles has been developed. The reaction exhibits broad substrate scope and provides efficient access to cyclohexene derivatives with good to excellent yields. A reasonable mechanism involving a metal-free thermal reversible process is proposed.

Palladium-catalyzed direct carboxylation of aryl bromides with carbon dioxide

(Chemical Equation Presented) A novel protocol for the direct carbon dioxide insertion (CO2) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO2, there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and in contrast to the well-established carbonylation processes, our protocol does not use highly toxic CO for the preparation of benzoic acids. Furthermore, this method is distinguished by its mild conditions, allowing the tolerance of a wide range of functional groups and substitution patterns. The crucial step of the process involves a challenging catalytic CO2 insertion into Pd-C bonds. Copyright

BF3·OEt2 promotes fast, mild, clean and regioselective dehydration of tertiary alcohols

BF3·OEt2 in methylene chloride at 25°C for 2 hours or less is shown to be effective for easy conversion of tertiary alcohols into the corresponding thermodynamically most stable alkenes.

Reactivity of Aryl Vinyl Di-?-methane Systems. Mechanistic and Exploratory Organic Photochemistry

The di-?-methane rearrangement of a series of meta and para substituted arylvinylmethane reactants was investigated with the aim of determiningthe patterns of reactivity in systems in which initial excitation is localized in the aryl moiety.Thus the photo