83469-17-4

Upstream product

• 126-81-8 dimedone 
• 106-96-7 propargyl bromide 

Downstream Products

• 117926-52-0 C₂₂H₂₂O₂ 
• 1321908-53-5 2-(4-(hydroxymethyl)pent-4-en-2-ynyl)-5,5-dimethyl-2-(prop-2-ynyl)cyclohexane-1,3-dione 

Relevant academic research and scientific papers

Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

A novel bis-1,4-disubstituted-1,2,3-triazole chemosensor, accessed with “Click Chemistry”, was probed for its recognition of metal ions. The interaction of the sensor with various cation analytes was investigated by 1H-NMR, UV–Vis absorption an

A Rh(I)-Catalyzed Cascade Cyclization of 1,5-Bisallenes and Alkynes for the Formation of cis-3,4-Arylvinyl Pyrrolidines and Cyclopentanes

The cascade cyclization reactions of 1,5-bisallenes grant access to a great variety of products by precisely tuning the catalyst system and/or the reagents involved. Herein, we present our findings that 1,5-bisallenes react with two molecules of dimethyl acetylenedicarboxylate to afford, in a completely diastereoselective manner, cis-3,4-arylvinyl pyrrolidines and cyclopentanes. DFT calculations have been used to postulate a mechanism for the developed reaction which encompasses a [2+2+2] cycloaddition reaction of the two alkynes and the external double bond of one allene, followed by a cycloisomerization involving the internal double bond of the second allene. (Figure presented.).

Palladium-catalyzed silaborative carbocyclizations of 1,6-diynes

An addition/cyclization reaction of 1,6-diynes was developed for the synthesis of highly substituted 1,2-dialkylidenecycloalkanes. In this work, 1,6-diynes reacted with (dimethylphenylsilyl)pinacol-borane in the presence of a palladium catalyst to afford 1,2-dialkylidenecycloalkanes bearing silyl and boryl groups with a (Z,Z)-configuration in good to excellent yields. Moreover, the corresponding products could be easily converted into other synthetically useful compounds. This protocol provides an efficient and practical method of heteroelement-element linkage addition to the unsaturated 1,6-diynes.

Diversity-oriented approach to linearly fused spirocycles via strategic utilization of a [2+2+2] cycloaddition and the Diels-Alder reaction

We have demonstrated a simple and an efficient protocol for assembling a library of linearly fused spirocycles in a diversity-oriented manner by utilizing two sequential atom-economic reactions such as a [2+2+2] cycloaddition and the Diels-Alder (DA) reac

Iron(ii)-catalysed [2+2+2] cycloaddition for pyridine ring construction

We report a new, simple and air-stable iron(ii) complex pre-catalyst for the synthesis of substituted pyridines via a [2+2+2] cycloaddition between diynes and nitrile derivatives. The Royal Society of Chemistry 2014.

Gold catalysis: Domino reaction of En-diynes to highly substituted phenols

By Sonogashira coupling of 1,7-heptadiynes and 1,8-octadiynes with 2-iodoallyl alcohols, various substrates that bear a 2-alkynylallyl alcohol moiety tethered to an additional alkyne were prepared in one step. Subjection to nitrogen acyclic carbene (NAC)/gold(I) catalysts delivered highly substituted phenols in an efficient domino reaction. Furan derivatives were formed as intermediates; this was proven by in situ NMR spectroscopy. The uncommon substitution pattern of these furans opens the way for a selective formation of phenols that contain the hydroxyl group in the meta position to the ring junction, which previously was not possible by gold-catalyzed furan-yne cyclization. Furthermore, interesting mechanistic insights were obtained by products derived from secondary allyl alcohols. In this case, in addition to the phenolic compounds, a ketone is formed by 1,2-alkyl shift.

Rhodium-catalysed -Cycloadditions of Acteylenes

Wilkinson's catalyst (0.5-2 molpercent) catalyses the chemospecific -cycloaddition of hepta-1,6-diynes with monoynes to give polysubstituted benzene derivatives in moderate to good yield.The reaction is favoured by polar solvents such as ethanol and occurs at 0-78 deg C.Several examples of intramolecular -cycloadditions of triynes are described and a mechanism that accounts for the chemospecificty and observed variations in rates of reaction is discussed.