172607-53-3

Upstream product

• 6919-61-5 N-methoxy-N-methylbenzamide 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 13047-06-8 o-bromobenzophenone 
• 1066-54-2 trimethylsilylacetylene 
• 108-86-1 bromobenzene 
• 133776-41-7 anthranilic acid N-methoxy-N-methylamide 
• 611-74-5 N,N-dimethylbenzamide 
• 71-43-2 benzene 
• 98-88-4 benzoyl chloride 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 25187-00-2 2-iodobenzophenone 
• 118-48-9 isatoic anhydride 

Downstream Products

• 172607-54-4 4-Methyl-1-phenyl-1-(2-trimethylsilanylethynyl-phenyl)-pent-4-en-2-yn-1-ol 
• 1309688-94-5 C₁₈H₁₉NSi 
• 676541-15-4 1-ethynyl-2-(1-phenylvinyl)benzene 
• 1638606-76-4 1-(cyclopropylidene(phenyl)methyl)-2-ethynylbenzene 
• 172607-60-2 5-(2-Ethynyl-phenyl)-2-methyl-5-phenyl-penta-2,3,4-trienal 
• 13225-63-3 2,3-Dihydro-4-phenyl-1H-benzindene 

Relevant academic research and scientific papers

A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership

An efficient, mild and rapid synthesis of α-fluoroketones has been developed, via a fruitful association between gold and Selectfluor starting from aldehyde-yne and alkynylaryl ketone derivatives. Several functionalized and synthetically highly valuable α-fluoroketones (21 compounds, up to 92%) were isolated in good to excellent yields via a remarkable regioselective oxyfluorination reaction in EtOH/H2O at room temperature. We have shed some light on parts of the mechanism by reacting diphenylacetylene and aldehyde-yne with or without Selectfluor. The reaction most presumably occurs via a sequential gold-catalyzed regioselective hydration followed by the α-fluorination reaction, but the presence of aldehyde moiety is crucial for the reactivity of alkyne function. The fluoroketones were efficiently transformed to 4-fluoroisoquinolines (9 compounds, 82–95%) of high pharmaceutical interest. (Figure presented.).

Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives

A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.

Copper-catalyzed cascade cyclization of 1,5-enynes: Via consecutive trifluoromethylazidation/diazidation and click reaction: Self-assembly of triazole fused isoindolines

Copper-catalyzed cascade cyclization of 1,5-enynes with two types of hypervalent reagents was developed via consecutive trifluoromethylazidation/diazidation and intramolecular click reaction (CUAAC), providing one-pot self-assembly of triazole fused isoindolines bearing a trifluoromethyl or an azide moiety. Moreover, the construction of a trifluoromethylcyclopropyl unit, which has been considered as a metabolically stable replacement for a tert-butyl moiety and was difficult to access, was also achieved under trifluoromethylazidation conditions. All these reactions exhibited excellent chemoselectivity, good to excellent yields and broad functional group tolerance.

Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines

Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.

An indenone synthesis involving a new aminotransfer reaction and its application to dibenzopentalene synthesis

o-(Phenylethynyl)phenyllithiums, generated by treatment of o-(phenylethynyl)bromobenzenes with tBuLi, were quenched with N,N-dimethylcarboamides to afford various 2-phenylindenone derivatives in moderate to good yields upon acidic workup. The choice of lithiation reagents was critical. When n-butyllithium was used the yields were reduced. The N-alkyl groups in the carboamides were also important: quenching with N,N-diethylbenzamides also afforded 2,3-diphenylindenones as the sole isolated products, but quenching with N-benzoylpiperidine led to 2-benzoyltolane in good yield. Control experiments revealed that the reactions proceed through a multi-step reaction sequence involving a novel intramolecular transamination to the α-acetylenic carbon of the alkynyl group. The method was applicable to the synthesis of dibenzopentalene derivatives as well as various indenone derivatives. A mechanism for the reaction is discussed.

Synthesis of isoindole derivatives by palladium-catalyzed domino reaction of (2-alkynyl)phenylketone o-pentafluorobenzoyloximes

Isoindole derivatives were synthesized by the palladium-catalyzed cyclization of (2-alkynyl)phenylketone O-pentafluoro-benzoyloximes in the presence of organometallic compounds such as sodium formate and aryl boronic acid. Georg Thieme Verlag Stuttgart - New York.

A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition

A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive β-lactone enolates via a pathway not involving the enolization of the corresponding β-lactones. The [2 + 2] cycloaddition of ynolate anions with δ- or σ-keto esters, followed by Dieckmann condensation, gives bicyclic β-lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.

INTRAMOLECULAR CYCLIZATION OF ENYNE CUMULENALS

Enyne cumulenals have been shown to undergo a Bergman cyclization or an intramolecular cycloaddition depending on the nature of substituents on the yne carbon.A hydrogen substituted cumulenal is cleanly converted to a naphthalene product while