1231248-07-9

Upstream product

• 25152-47-0 2,2-diphenyl-1-methylenecyclopropane 
• 1008-89-5 2-phenylpyridine 
• 5957-89-1 2-(2-methoxy-phenyl)-pyridine 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 74190-01-5 1-iodo-2-(prop-2-en-1-yl)benzene 
• 42918-20-7 1-allyl-2-bromobenzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates

A palladium-catalyzed intramolecular Mizoroki-Heck-type reaction of diarylmethyl tert-butyl carbonates has been developed. The reaction proceeds under external base-free, neutral conditions to form the corresponding methyleneindanes in good yields only with liberation of CO2 and tBuOH. The resulting exo-methylene moiety is reactive and thus a good synthetic handle for further manipulations. Additionally, the asymmetric synthesis is also possible through a Pd/chiral Mandyphos ligand-mediated kinetic resolution. To the best of our knowledge, this is the first successful example of catalytic enantioselective Mizoroki-Heck-type reaction of secondary benzyl electrophiles. (Figure presented.).

The Pd-catalyzed synthesis of benzofused carbo- and heterocycles through carbene migratory insertion/carbopalladation cascades with tosylhydrazones

The Pd-catalyzed reaction between o-iodoallylbenzene and tosylhydrazones gives rise to indene derivatives through a process that involves a carbene migratory insertion followed by an intramolecular carbopalladation, with the formation of two C-C bonds on

Ruthenium-catalyzed hydroarylation of methylenecyclopropanes through C-H bond cleavage: Scope and mechanism

Intermolecular hydroarylation reactions of highly strained methylenecyclopropanes 2-phenylmethylenecyclopropane (1), 2,2- diphenylmethylenecyclopropane (2), methylenespiropentane (3), bicyclopropylidene (4), (dicyclopropylmethylene)cyclopropane (5), and benzhydrylidenecyclopropane (6) through C-H bond functionalization of 2-phenylpyridine (7 a) and other arenes with directing groups were studied. The reaction was very sensitive to the substitution on the methylenecyclopropanes. Although these transformations involved (cyclopropylcarbinyl)-metal intermediates, substrates 1 and 4 furnished anti-Markovnikov hydroarylation products with complete conservation of all cyclopropane rings in 11-93 % yield, whereas starting materials 3 and 5 were inert toward hydroarylation. Methylenecyclopropane 6 formed the products of formal hydroarylation reactions of the longest distal C-C bond in the methylenecyclopropane moiety in high yield, and hydrocarbon 2 afforded mixtures of hydroarylated products in low yields with a predominance of compounds that retained the cyclopropane unit. As byproducts, Diels-Alder cycloadducts and self-reorganization products were obtained in several cases from substrates 1-3 and 5. The structures of the most important new products have been unambiguously determined by X-ray diffraction analyses. On the basis of the results of hydroarylation experiments with isotopically labeled 7 a-[D5], a plausible mechanistic rationale and a catalytic cycle for these unusual ruthenium-catalyzed hydroarylation reactions have been proposed. Arene-tethered ruthenium-phosphane complex 53, either isolated from the reaction mixture or independently prepared, did not show any catalytic activity. Copyright

Efficient Br?nsted acid catalyzed hydrations and hydroaminations of (dicyclopropylmethylene)cyclopropane

(Dicyclopropylmethylene)cyclopropane underwent efficient Br?nsted acid catalyzed hydrations and hydroaminations with H2O and basic amines, respectively, occurring with conservation of all three cyclopropane rings. Georg Thieme Verlag Stuttgart