1574-79-4

Upstream product

• 1595-64-8 1,5-diphenyl-penta-2,4-diyn-1-ol 
• 879560-02-8 (1,1-dibromobut-1-en-3-yn-2-yl)benzene 
• 98-88-4 benzoyl chloride 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 536-74-3 phenylacetylene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 15814-30-9 1,5-diphenyl-penta-1,4-diyn-3-one 
• 1431620-35-7 (S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol 

Downstream Products

• 1246055-06-0 1,5-diphenyl-penta-2,4-diyn-1-one tosylhydrazone 
• 29113-75-5 2,5-diphenyl-furan-3-carboxylic acid 
• 84302-12-5 methyl 2,5-diphenylfuran-3-carboxylate 

Relevant academic research and scientific papers

Gold-Catalyzed Oxidative Cyclization Involving Nucleophilic Attack to the Keto Group of α,α′-Dioxo Gold Carbene and 1,2-Alkynyl Migration: Synthesis of Furan-3-carboxylates

A multicomponent strategy for the synthesis of functionalized furan-3-carboxylates based on gold-catalyzed oxidative cyclization of diynones with alcohols or water has been developed. Mechanistic studies revealed that a rare nucleophilic attack to the carbonyl group of the α,α′-dioxo gold carbene instead of the carbene center and 1,2-alkynyl group migration were involved in this transformation. This method offers several advantages such as mild conditions, high regio- and chemoselectivity, and wide functional group compatibility.

Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.

Ethyl lactate as a renewable carbonyl source for the synthesis of diynones

Ethyl lactate, a sustainable feedstock, serves as a highly attractive building block for the synthesis of value-added chemicals such as skipped diynones and, after gold-catalyzed transposition, conjugated diynones. Green solvents are involved in all steps

Gold-catalyzed 1,3-transposition of ynones

An efficient, regioselective gold-catalyzed 1,3-transposition reaction of ynones and diynones has been developed. It was found that stereoelectronic (interrupted conjugation) and electronic (extended conjugation) factors could efficiently govern the regio

Synthesis of simple diynals, diynones, their hydrazones, and diazo compounds: Precursors to a family of dialkynyl carbenes (R1-C-C- C-C-C-R2)

A variety of substituted pentadiynols, -diynals, and -diynones have been prepared en route to precursors to dialkynyl carbenes (R1-C-C-C- C-C-R2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4 + 1, 3 + 2, 2 + 2 + 1, and 2 + 1 + 1 + 1 coupling methodologies. The Dess-Martin periodinane serves as an excellent method for the oxidation of pentadiynols to diynals and diynones, although many of the oxidized products are sufficiently reactive that they were not isolated; rather, they were generated in situ and intercepted with nucleophiles such as tosylhydrazide or trisylhydrazide. The hydrazone derivatives are generally reliable precursors to diazo compounds and carbenes, although cyclization of the hydrazone to afford a pyrazole can be a complicating factor in certain instances.

One-pot formation and derivatization of di- and triynes based on the Fritsch-Buttenberg-Wiechell rearrangement

(Chemical Equation Presented) A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement is used to gene

A one-pot synthesis and functionalization of polyynes

A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li-acetylide is then trapped in situ with an electrophile to pro