68376-08-9

Upstream product

• 26260-02-6 2-iodobenzaldehyde 
• 1436869-06-5 1,3-diphenylcyclobut-2-enol 
• 98-80-6 phenylboronic acid 
• 28215-42-1 (3-hydroxy-naphthalen-2-yl)-phenyl-methanone 
• 612-12-4 o-Xylylene dichloride 
• 120-46-7 1,3-diphenylpropanedione 
• 1393090-01-1 tert-butyl 3-phenyl-1-(2-(phenylethynyl)phenyl)prop-2-ynyl carbonate 

Relevant academic research and scientific papers

Palladium-Catalyzed Ring-Opening Coupling of Cyclobutenols with Aryl Halides

A palladium(0)-catalyzed ring-opening cross-coupling reaction between tert -cyclobutenols and aryl halides produces γ-arylated β,γ-unsaturated ketones. In the case of aryl halides bearing functional groups at the ortho position, the resulting ring-opened ketones undergo intramolecular condensation to afford bicyclic aromatic compounds.

Hydrogen Bonding Networks Enable Br?nsted Acid-Catalyzed Carbonyl-Olefin Metathesis**

Synthetic chemists have learned to mimic nature in using hydrogen bonds and other weak interactions to dictate the spatial arrangement of reaction substrates and to stabilize transition states to enable highly efficient and selective reactions. The activation of a catalyst molecule itself by hydrogen-bonding networks, in order to enhance its catalytic activity to achieve a desired reaction outcome, is less explored in organic synthesis, despite being a commonly found phenomenon in nature. Herein, we show our investigation into this underexplored area by studying the promotion of carbonyl-olefin metathesis reactions by hydrogen-bonding-assisted Br?nsted acid catalysis, using hexafluoroisopropanol (HFIP) solvent in combination with para-toluenesulfonic acid (pTSA). Our experimental and computational mechanistic studies reveal not only an interesting role of HFIP solvent in assisting pTSA Br?nsted acid catalyst, but also insightful knowledge about the current limitations of the carbonyl-olefin metathesis reaction.

Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade

A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).

Gold-Catalyzed Oxidative Cyclizations of { o-(Alkynyl)phenyl propargyl} Silyl Ether Derivatives Involving 1,2-Enynyl Migration: Synthesis of Functionalized 1 H-Isochromenes and 2 H-Pyrans

A new and convenient strategy for the synthesis of functionalized 1H-isochromene and 2H-pyran derivatives based on gold-catalyzed oxidative cyclizations of o-(alkynyl)phenyl propargyl ether derivatives has been developed. The reaction proceeds via gold-catalyzed highly regioselective oxidation, followed by 1,2-migration of an enynyl group and nucleophlic addition. Isocoumarins were also constructed through oxidative cleavage of the exocyclic double bond of the obtained 1H-isochromenes.

Generation of o-quinodimethanes (o-QDMs) from benzo[c]oxepines and the synthetic application for polysubstituted tetrahydronaphthalenes

A novel method for the generation of o-quinodimethane (o-QDM) intermediates is reported using a mild and efficient base-promoted ring-opening of benzo[c]oxepines. Among the benzo[c]oxepines studied, indanone containing analogues demonstrated the greatest

Direct synthesis of substituted naphthalenes from 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzenes including a novel rearrangement aromatization of benzo[ c ]oxepine

An unexpected rearrangement aromatization of benzo[c]oxepine has been revealed to synthesize substituted naphthalenes. This observation was further exploited to develop an efficient approach for the construction of naphthalenes from simple and commercially available 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzene compounds via a new domino reaction sequence.

Gold-catalyzed cascade cyclizations of 1,6-diynyl carbonates to benzo[b]fluorenes involving arylation of oxocarbenium ion intermediates and decarboxylative etherification

Rearranged: The described gold-catalyzed cycloisomerizations give access to highly substituted benzo[b]fluorenes under mild reaction conditions (see scheme). Experimental results indicate that the in situ formed oxocarbenium ion intermediates, derived from gold-catalyzed 3,3-rearrangement and 6-endo-dig cyclization, undergo intramolecular arylation and subsequent decarboxylative etherification to furnish the final ether products. Copyright

Synthesis of 2-acyl-3-arylnaphthalenes by dual catalysis of sodium tetrachloroaurate toward alkyne-propargylic acetates

A new and highly convenient Au-catalyzed cyclization of alkyne-propargylic acetates leading to 2-acyl-3-arylnaphthalene derivatives is described; these are possible candidates for light-emitting materials. Georg Thieme Verlag Stuttgart.