4165-81-5

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 111, p. 9119, 1989 DOI: 10.1021/ja00207a029The Journal of Organic Chemistry, 52, p. 1695, 1987 DOI: 10.1021/jo00385a009

Upstream product

• 119-61-9 benzophenone 
• 13154-14-8 1-propenylmagnesium bromide 
• 15295-29-1 4,4-diphenyl-4-hydroxybut-2-ene 
• 4165-79-1 1,1-diphenyl-3-buten-1-ol 
• 46970-87-0 DHP-362 
• 625-38-7 but-3-enoic acid 
• 25152-47-0 2,2-diphenyl-1-methylenecyclopropane 
• 6317-10-8 2,2-diphenyl-1,3-dithiolane 
• 23719-80-4 cyclopropylmagnesium bromide 
• 13633-26-6 4-phenylbut-1-en-3-yne 
• 54709-17-0 3-(2,2-Diphenylcyclopropyl)-3-methyl-1,1-diphenyl-1-buten 
• 591-87-7 Allyl acetate 
• 525-06-4 diphenyl ketene 
• 35466-83-2 allyl methyl carbonate 

Downstream Products

• 5171-94-8 1-(2,2-Diphenyl-vinyl)-2,2,3,3-tetracyan-cyclobutan 
• 5171-95-9 3,3-Diphenyl-4,4,5,5-tetracyan-cyclohexen 
• 65115-99-3 1,1-Dimethoxy-2-(2,2-diphenylvinyl)cyclopropan 
• 15517-62-1 1,1-Dicyano-4,4-diphenyl-1,3-butadien 
• 36748-71-7 3-Phenyl-4-cyclohexen-1,1,2,2-tetracarbonitril 
• 100036-15-5 4-(2,2-Diphenyl-vinyl)-2,2-bis-trifluoromethyl-cyclobutane-1,1-dicarbonitrile 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 
• 26929-50-0 4-Methoxy-4,4-diphenyl-but-1-en 
• 57766-99-1 3-Methoxy-1,1-diphenyl-but-1-en 
• 119296-85-4 (E)-1,1-diphenyl-1-methoxy-2-butene 
• 867267-57-0 [Rh(triphenylphosphine)2(CO)(CH₃CHCHCPh₂)] 
• 1016648-01-3 C₂₆H₃₂N₄ 
• 1198573-95-3 methyl 2-(2,2-diphenylvinyl)-1-(pyrrolidin-1-ylcarbonyl)cyclopropanecarboxylate 
• 1262436-54-3 C₂₄H₃₂N₂O₂S 

Relevant academic research and scientific papers

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis

Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy

Neodymium-Promoted Highly Selective Carbon-Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

The carbon-carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

Transition-Metal-Free Allylic Borylation of 1,3-Dienes

This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

Palladium-Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3-Dienes via C—H Bond Activation: Efficient Access to 3,4-Dihydroisocoumarin and 5,6-Dihydrocoumalins

We report a palladium-catalyzed formal intermolecular [4+2] cycloaddition of benzoic and acrylic acids with 1,3-dienes including the stock chemicals 1,3-butadiene and isoprene leading to synthetically useful 3,4-dihydroisocoumarins and 5,6-dihydrocoumalins. Stepwise C—H bond cleavage and annulation are likely involved in the reaction pathway. The synthetic potential of the methodology was demonstrated by two short derivatizations and total synthesis of natural product Clausamine B.

Transition-metal-free synthesis of vicinal triborated compounds and selective functionalisation of the internal C-B bond

1,2,3-Triborated compounds can be prepared by simple nucleophilic borylation of 1,3-dienes, without the assistance of metal catalysts. Selective functionalisation of the internal C-B bond of the 1,2,3-triborated compounds, through cross-coupling with aryl

Hypervalent Iodine(III)-Mediated Oxidative Fluorination of Alkylsilanes by Fluoride Ions

The first example of a hypervalent iodine(III)-mediated oxidative fluorination of alkylsilanes by fluoride ions without the use of transition metals is demonstrated. This reaction is operationally simple, scalable, and proceeds under mild reaction conditions. Mechanistic studies suggest the involvement of a single-electron transfer resulting from the interaction of an organopentafluorosilicate and aryliodonium difluoride, which were generated in situ from the corresponding alkylsilane and iodosobenzene, respectively, in the presence of fluoride ions.