59046-69-4

Upstream product

• 59046-72-9 o-(phenylethynyl)benzaldehyde 
• 1530-33-2 isopropyltriphenylphosphonium bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 536-74-3 phenylacetylene 
• 24470-78-8 isopropyltriphenylphosphonium iodide 

Downstream Products

• 1238892-93-7 1-(2-methoxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-95-9 1-(2-methoxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-98-2 1-(2-ethoxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-99-3 1-(2-ethoxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-96-0 1-(2-hydroxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-79-9 2-phenyl-1-(prop-1-en-2-yl)-1H-indene 
• 1238892-80-2 2-phenyl-1-(prop-1-en-2-yl)-1H-indene 
• 1238892-97-1 1-(2-hydroxypropan-2-yl)-2-phenyl-1H-indene 
• 1238892-78-8 2-phenyl-1-(prop-1-en-2-yl)-1H-indene 
• 1238893-00-9 1-(2-(allyloxy)propan-2-yl)-2-phenyl-1H-indene 
• 1238893-01-0 1-(2-(allyloxy)propan-2-yl)-2-phenyl-1H-indene 
• 1238893-02-1 1-(2-iso-propoxypropan-2-yl)-2-phenyl-1H-indene 
• 1078710-90-3 2,2-dimethyl-3-[2-(2-phenyl-1-ethynyl)phenyl]oxirane 

Relevant academic research and scientific papers

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Palladium-Catalyzed Dialkylation of C-C Triple Bonds: Access to Multi-Functionalized Indenes

A palladium-catalyzed dialkylation of 1,3-dien-5-ynes was developed using alkenyl double bonds as the initiator and terminator for the synthesis of functionalized indene derivatives. The reactions were performed under mild reaction conditions, affording the corresponding multi-substituted indene derivatives in high efficiency via unprecedented 5-endo cyclization and alkylation processes. It was found that the substituent location at the alkenyl double bond was essential for the chemoselective synthesis of the indene and naphthalene derivatives, respectively.

A gold(i)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes

A novel gold(i)-catalyzed intramolecular tandem cyclization reaction of ortho-(arylethynyl)arenemethylenecyclopropanes provided an efficient approach to prepare functionalized 11H-benzo[a]fluorene derivatives in moderate to good yields. Further transformations as well as applications of the products have been presented and a plausible reaction mechanism has also been proposed on the basis of deuterium labeling and control experiments.

Gold(I)-catalyzed cycloisomerizations and alkoxycyclizations of ortho-(alkynyl)styrenes

Indenes and related polycyclic structures have been efficiently synthesized by gold(I)-catalyzed cycloisomerizations of appropriate ortho-(alkynyl)styrenes. Disubstitution at the terminal position of the olefin was demonstrated to be essential to obtain products originating from a formal 5-endo-dig cyclization. Interestingly, a complete switch in the selectivity of the cyclization of o-(alkynyl)-a-methylstyrenes from 6-endo to 5-endo was observed by adding an alcohol to the reaction media. This allowed the synthesis of interesting indenes bearing an all-carbon quaternary center at C1. Moreover, dihydrobenzo[a]fluorenes can be obtained from substrates bearing a secondary alkyl group at the β-position of the styrene moiety by a tandem cycloisomerization/1,2-hydride migration process. In addition, diverse polycyclic compounds were obtained by an intramolecular gold-catalyzed alkoxycyclization of o-(alkynyl)styrenes bearing a nucleophile in their structure. Finally, the use of a chiral gold complex allowed access to elusive chiral 1H-indenes in good enantioselectivities.

Gold-catalyzed oxidative cyclizations of 2-oxiranyl-1-alkynylbenzenes for diastereoselective synthesis of highly substituted 2-hydroxyindanones

We report the gold-catalyzed oxidative cyclizations of 2-oxiranyl-1- alkynylbenzenes into highly substituted 2-hydroxyindanone frameworks bearing a tertiary alcohol. Such gold-catalyzed reactions comprise an initial internal redox reaction, sulfoxide oxidation of α-carbonyl gold-carbenoids, followed by gold-catalyzed formal ene reactions on the resulting diketone intermediates. Copyright

Gold(I)-catalyzed enantioselective synthesis of functionalized indenes

Chemical Equation Presented Can you dig it? An asymmetric synthesis of functionalized 1H-indenes from easily available ortho-(alkynyl)styrene derivatives under mild reaction conditions has been achieved. The reactions proceed through an unprecedented and selective 5-endo-dig gold(l)-catalyzed cycloisomerization or alkoxycyclization, if water or an alcohol is present (see scheme).

Halocyclization of o-(alkynyl)styrenes. Synthesis of 3-halo-1H-indenes

o-(Alkynyl)styrenes undergo halocarbocyclization processes via a 5-endo-dig ring closure. By this strategy an efficient synthesis of 3-halo-1H-indene derivatives has been developed.