6936-14-7

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 5720-05-8 4-methylphenylboronic acid 
• 123994-49-0 3,4-dihydro-1-naphthyl triflate 
• 101552-29-8 1-methyl-4-(1-phenylbuta-1,3-dienyl)benzene 
• 1064664-64-7 1-methyl-4-(4-phenylbut-1-yn-1-yl)benzene 
• 5142-75-6 tri(p-tolyl)bismuth 
• 149512-01-6 1,2-dihydro-4-iodonaphthalene 
• 17336-59-3 1-tetralone tosylhydrazone 
• 19455-84-6 3,4-dihydronaphthalen-1-yl acetate 
• 106-38-7 para-bromotoluene 
• 27331-24-4 1-phenyl-4-(p-tolyl)buta-1,3-diene 

Downstream Products

• 109036-36-4 1,2-epoxy-1-p-tolyl-1,2,3,4-tetrahydro-naphthalene 
• 27331-34-6 1-(4-methylphenyl)naphthalene 
• 108973-38-2 3-nitro-4-p-tolyl-1,2-dihydro-naphthalene 
• 19723-03-6 7-methyl-1-phenylnaphthalene 
• 29304-61-8 6-methyl-1-phenylnaphthalene 
• 29304-62-9 6-methyl-4-phenyl-1,2-dihydro-naphthalene 
• 29304-60-7 7-methyl-4-phenyl-1,2-dihydronaphthalene 
• 108973-58-6 1-p-tolyl-1,2,3,4-tetrahydro-[2]naphthylamine 
• 109036-39-7 1-(p-tolyl)-3,4-dihydronaphthalen-2(1H)-one 

Relevant academic research and scientific papers

Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate

A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling

The Suzuki-Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C-C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

Olefin Preparation via Palladium-Catalyzed Oxidative De-Azotative and De-Sulfitative Internal Cross-Coupling of Sulfonylhydrazones

A novel reactivity of sulfonylhydrazones under Pd catalysis is described, where SO2 and N2 are formally extruded to afford the product of an apparent internal coupling reaction. The reaction is effective with both carbocyclic and heterocyclic aromatic precursors.

Atom-efficient vinylic arylations with triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis

The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times.

FeCl3-catalyzed intramolecular hydroarylation of alkynes

The intramolecular hydroarylation of alkynes using a substoichiometric amount of FeCl3 is described. When starting from tetrasubstituted substrates, products resulting from an unexpected toluene (or xylene) elimination are isolated in good yields.

Palladium-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates

The cross-coupling reaction of 9-alkyl-9-borabicyclononane (9-R-9-BBN), 1-alkenyl-1,3,2-benzodioxaborole, or aryl boronic acid with 1-alkenyl or aryl triflates in the presence of K3PO4 (1.5 equiv) and a catalytic amount of Pd(PPh3)4 or Cl2Pd(dppf) resulted in high yields.The reaction conditions are sufficiently mild so that a variety of functionalized alkenes, alkadienes, and arenes are readily obtained.The utility of the present reaction was demonstrated by the cyclization of ω-alkenyl triflates leading to a benzo-fused cycloalkene and bicyclic alkene via a hydroboration intramolecular coupling sequence.

Thermolysis of Phenyl-substituted 1,2-Dihydronaphthalenes. Evidence for Diphenylbutadienes as Intermediates

The thermal rearrangement of the four phenyl-substituted 1,2-dihydronaphthalenes (15), (16), (19), and (20) have been studied by flash vacuum pyrolysis (FVP).By using the deuteriated starting compounds -(15) and -(16), it has been established that 1- and 4-phenyl-1,2-dihydronaphthalene (15) and (19) and 2- and 3-phenyl-1,2-dihydronaphthalene (16) and (20) are interconverted via the intermediates 1- and 2-phenyl-2,3-dihydronaphthalene (17) and (18), respectively, through two consecutive, sigmatropic 1,5-hydrogen shifts.In both processes partial oxidation to the corresponding phenylnaphthalenes (21) and (22) takes place.The deuterium distribution in the pyrolysis products suggests that in the hot zone diphenylbutadienes are formed, which are reconverted into phenyldihydronaphthalenes upon reaching the cold receiving flask.By FVP of 4-(p-tolyl)-1,2-dihydronaphthalene (34), 1-phenyl-1-(p-tolyl)butadiene (39), and 1-phenyl-4-(p-tolyl)butadiene (45) the latter type of interconversion could be confirmed.