171258-05-2

Upstream product

• 917-92-0 3,3-Dimethylbut-1-yne 
• 2142-69-0 2-bromophenyl methyl ketone 
• 2142-70-3 2-iodoacetophenone 
• 1441-97-0 2'-(methylthio)acetophenone 
• 772-38-3 4-tert-Butylphenylacetylene 

Downstream Products

• 371964-03-3 tert-butyl-{1-[2-(3,3-dimethyl-but-1-ynyl)-phenyl]-vinyloxy}-dimethyl-silane 
• 51595-06-3 2-tert-butyl-1,4-naphthoquinone 
• 1394123-34-2 C₂₂H₂₂O 

Relevant academic research and scientific papers

Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones

An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms?-?a 5-exo-dig or a 6-endo-dig cyclization-leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence of ammonium acetate, the two intermediate compounds undergo further rearrangement to 2,3-disubstituted indenones and 1,3-disubstituted isoquinolines, respectively. While both reaction pathways proceed via a cyclization-rearrangement cascade, the gold-mediated 5-exo-dig process is especially notable, as it provides a novel cyclization protocol of 2-alkynylarylketones.

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives

An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.

CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones: Efficient synthesis of 1,4-naphthoquinones

A concise and efficient method for the synthesis of 1,4-naphthoquinones has been successfully developed involving a CuI/Cu(OTf)2/DMSO system-catalyzed intramolecular oxidative cyclization of (o-alkynyl)arylketones. The present protocol provided a novel approach to access functionalized 1,4-naphthoquinones from non-naphthoquinone precursors with good selectivity and functional group tolerance.

A rhodium-catalysed Sonogashira-type coupling exploiting C-S functionalisation: Orthogonality with palladium-catalysed variants

This report concerns the development of an efficient Sonogashira-type coupling of arylmethylsulfides and terminal alkynes to generate aryl alkyne motifs. Orthogonal reactivity between traditional Pd catalysts, and the Rh catalysts employed, results in the ability to selectively activate either the C-S bond or C-X bond through catalyst choice. The Rh-bisphosphine catalyst has further been shown to be able to effect a hydroacylation-Sonogashira tandem sequence, and in combination with further onward reactions has been used in the synthesis of heterocycles and polycyclic systems.

Asymmetric Hydrogenation of In Situ Generated Isochromenylium Intermediates by Copper/Ruthenium Tandem Catalysis

The first asymmetric hydrogenation of in situ generated isochromenylium derivatives is enabled by tandem catalysis with a binary system consisting of Cu(OTf)2 and a chiral cationic ruthenium–diamine complex. A range of chiral 1H-isochromenes were obtained in high yields with good to excellent enantioselectivity. These chiral 1H-isochromenes could be easily transformed into isochromanes, which represent an important structural motif in natural products and biologically active compounds. The chiral induction was rationalized by density functional theory calculations.

Cu(0)/Selectfluor System-Mediated Mild Synthesis of Fluorinated Fluorenones from Nonaromatic Precursors (1,6-Enynes) Involving C-C Single Bond Cleavage

A novel and facile method for the mild construction of fluorinated fluorenones from nonaromatic precursors (1,6-enynes) mediated by a Cu(0)/Selectfluor system has been successfully achieved. Preliminary mechanistic investigations indicate that the reactio

Palladium-catalyzed selective synthesis of naphthalenes and indenones and their luminescent properties

Selective synthesis of functionalized naphthalenes and indenones by palladium-catalyzed cyclization of o-haloacetophenones and terminal alkynes in the presence of a secondary amine is reported. Under a nitrogen atmosphere, the palladium-catalyzed reaction

Transition-metal-promoted 6-endo-dig cyclization of aromatic enynes: Rapid synthesis of functionalized naphthalenes

Transition-metal-mediated cyclization of aromatic enynes provides high yields of sustituted naphtalene compounds. The reduction can tolerate a wide range of substituents on both the olefin and the alkyne. The most useful catalysts were found to be [Rh(CO)

General Preparation of 3-Alkyl-1-Naphthols

Potassium enolates derived from readily available o-alkynylacetophenones undergo intramolecular cycloaromatization on heating to afford 3-alkyl-1-naphthols in good yields. - Key words: Cycloaromatization, enynone, ynenone, 3-alkyl-1-naphthol.