119082-40-5

Upstream product

• 946401-55-4 7-phenylhept-3-yne-2,5-diol 
• 64-04-0 phenethylamine 
• 106-38-7 para-bromotoluene 
• 1222465-56-6 trans-5-hydroxy-7-phenylhept-3-en-2-one 
• 37904-38-4 5-phenylpent-1-en-3-ol 
• 104-53-0 3-phenyl-propionaldehyde 
• 113767-83-2 (E)-1-Phenyl-4-(toluene-4-sulfonyl)-hept-5-en-3-ol 

Relevant academic research and scientific papers

Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions

A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.

Synthesis of multisubstituted furans via copper-catalyzed intramolecular O-vinylation of ketones with vinyl bromides

With the catalysis of CuI/3,4,7,8-tetramethyl-1,10-phenanthroline, various ketones smoothly underwent the intramolecular O-vinylation with vinyl bromides leading to the efficient synthesis of the corresponding multisubstituted furans.

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.

Synthesis of furans, pyrroles and pyridazines by a ruthenium-catalysed isomerisation of alkynediols and in situ cyclisation

Alkyne-1,4-diols are readily available substrates which are isomerised to 1,4-diketones using Ru(PPh3)3(CO)H2/xantphos as a catalyst. In situ cyclisation into furans, pyrroles and pyridazines has been achieved under suitable conditions.

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.

Ruthenium-catalysed conversion of 1,4-alkynediols into pyrroles

Various 1,2,5-substituted pyrroles have been synthesised from 1,4-alkynediols using a ruthenium catalysed isomerisation to give the corresponding 1,4-dicarbonyl compounds, which undergo in situ cyclisation to pyrroles in the presence of amine.

A Convenient Method for the Preparation of Furan and Pyrrole Derivatives via Palladium(II)-Catalyzed Intramolecular Cyclization of 3- and 4-Alkenyl Alcohol or Amine Derivatives

Several furan and pyrrole derivatives were prepared through palladium(II)-catalyzed intramolecular cyclization of 2-(p-toluenesulfonyl)-3-butenols and 2-methanesulfonyl-4-pentenyl alcohol or amine derivatives in good yields.