1222-76-0

Upstream product

• 4747-13-1 α-methoxystyrene 
• 31984-10-8 1-bromo-4-phenylbutan-2-one 
• 100-52-7 benzaldehyde 
• 118584-91-1 5-phenylpent-1-yn-3-one 
• 106-38-7 para-bromotoluene 
• 1222465-67-9 trans-4-hydroxy-1,6-diphenylhex-2-en-1-one 
• 541507-39-5 (3-allyloxy-pent-4-enyl)-benzene 
• 541507-18-0 2-phenethyl-2,3-dihydrofuran 
• 191112-45-5 2-(2'-phenylethyl)-2,5-dihydrofuran 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 1226-96-6 1,6-diphenylhexane-1,4-dione 

Relevant academic research and scientific papers

Ru- and Pd-catalysed synthesis of 2-arylfurans by one-flask heck arylation/oxidation

2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disubstituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.

An expedient route to substituted furans via olefin cross-metathesis

The olefin cross-metathesis (CM) reaction is used extensively in organic chemistry and represents a powerful method for the selective synthesis of differentially substituted alkene products. Surprisingly, efforts to integrate this remarkable process into strategies for aromatic and heteroaromatic construction have not been reported. Such structures represent key elements of the majority of small molecule drug compounds; methods for the controlled preparation of highly substituted derivatives are essential to medicinal chemistry. Here we show that the olefin CM reaction, in combination with an acid cocatalyst or subsequent Heck arylation, provides a concise and flexible entry to 2,5-di- or 2,3,5-tri-substituted furans. These cascade processes portend further opportunities for the regiocontrolled preparation of other highly substituted aromatic and heteroaromatic classes.

2,5-Disubstituted furans from 1,4-alkynediols

1,4-Alkynediols serve as readily available starting materials for isomerisation to 1,4-diketones, which can be converted in situ into the corresponding furans by acid-catalysed dehydration. A range of 2,5-disubstituted furans was prepared using the ruthenium-based catalyst Ru(PPh3)3(CO)H2 with Xantphos at 1 mol % loading.

Preparation of 2,5-disubstituted furans from terminal ynones and aldehydes with CrCl2, Me3SiCl, and H2O

Treatment of α,β-acetylenic ketones with chromium(II) in the presence of aldehydes, Me3SiCl and water in THF gives 2,5-disubstituted furans in good to excellent yields.

Preparations of Furans from α-Bromo Ketones and Enol Ethers Catalyzed by a Rhenium(I) Nitrogen Complex

By the catalytic use of a rhenium(I) nitrogen complex, [ReCl(N2)(PMe2Ph)4], α-keto radicals are generated from α-bromo ketones and react with vinyl ethers and silyl enol ethers intermolecularly. Various substituted furans, including tetrasubstituted furans such as furoguaiacin, are prepared by this method.