13225-65-5

Upstream product

• 13225-61-1 1,7-diphenyl-4-oxahepta-1,6-diyne 
• 53877-63-7 (3-(prop-2-ynyloxy)prop-1-ynyl)benzene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1346682-29-8 1-phenyl-3-(3-phenylprop-2-ynyloxy)propan-2-one 
• 108-86-1 bromobenzene 
• 6921-27-3 dipropargyl ether 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

Triflic acid catalysed regioselective synthesis of substituted naphthalenes by benzannulation of carbonyls with alkynes

An interesting and facile triflic acid catalysed annulation of α-aryl carbonyls with arylalkynes is presented for the regioselective synthesis of substituted naphthalenes. The annulation reaction involves a sequence of electrophilic attack of carbonyl on arylalkyne and benzannulation catalysed by triflic acid. The present catalyst effects this transformation at room temperature itself. Intramolecular version of the present Br?nsted acid catalysis furnished compounds containing 1-arylnaphthalene core fused with ring systems in excellent yields.

Alumina-Mediated π-Activation of Alkynes

The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.

Sonogashira coupling and Garratt-Braverman cyclization in tandem: Formation of four C-C bonds leading to the synthesis of aryl dihydro isofurans and isoindoles

Abstract In this Letter we report an interesting one pot synthesis of aryl dihydro isofurans and isoindoles, naturally occurring privileged skeletons, in excellent yields from easily accessible starting materials. The process involved carrying out three reactions in a tandem manner leading to 4 C-C bond formations, namely two Sonogashira couplings (2 × 1 C-C bond) followed by Garratt-Braverman Cyclization (2 C-C bond).

Garratt-Braverman cyclization on basic alumina: A green protocol with improved selectivity

A green protocol (compared to the existing methodology) for carrying out Garratt-Braverman cyclization has been developed. The method involves stirring a pre-absorbed bispropargyl sulfone/ether/sulfonamide over basic alumina. The reaction with sulfones wa

Synthesis of arylnaphthalene lignan scaffold by gold-catalyzed intramolecular sequential electrophilic addition and benzannulation

An intramolecular approach to generate compounds containing an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and retrojusticidin B (Figure presented).

Intramolecular anionic Diels-Alder reactions of 1-aryl-4-oxahepta-1,6-diyne systems in DMSO

Base-promoted cycloaddition reactions of 1-aryl- or 1-aryl-7-substituted-4- oxahepta-1,6-diyne systems in DMSO have proven to involve an anionic intramolecular Diels-Alder process taking place even at room temperature in spite of the reaction suffering from temporary disruption of aromaticity. Although initially formed α-arylallenide anion can be protonated by DMSO, it can be back to the allenide anion probably because of a small acidity difference between α-arylallene and DMSO. The α-arylallenide anion in combination with the α-aryl substituent can constitute an anionic diene structure that undergoes the intramolecular Diels-Alder reaction involving the C(6)-yne part, a very fast process probably because of the increased HOMO-1 level of the anionic diene, as shown by DFT calculations. Diversified substituted naphthalenes, benzofurans, phenanthrenes, and quinolines, including biaryl architectures, are available from 4-oxahepta-1,6-diynes in a highly expeditious way.

Gold-catalyzed intramolecular [3 + 2]-cycloaddition of arenyne-yne functionalities

We report a new efficient intramolecular [3 + 2]-cycloaddition of unactivated arenyne (or enyne)-yne functionalities, catalyzed mainly by the AuPPh3SbF6 complex (2 mol %) under ambient conditions. The value of this cyclization is ref

Nickel-catalyzed cocyclotrimerization of arynes with diynes; a novel method for synthesis of naphthalene derivatives

The NiBr2(dppe)-Zn system effectively catalyzes the [2 + 2 + 2] cocyclotrimerization of arynes with diynes, leading to substituted naphthalene derivatives in moderate to good yields. This cocyclotrimerization reaction shows excellent tolerance of functional groups and leads to products of 5- to 7-membered fused-ring sizes. The Royal Society of Chemistry 2005.

Thermal and Au(I)-catalyzed intramolecular [4+2] cycloaddition of aryl-substituted 1,6-diynes for the synthesis of biaryl compounds

1,6-Diynes, possessing aryl groups on their termini, undergo an intramolecular [4+2] cycloaddition via strained cyclic allene intermediates to give various biaryl compounds. Under thermal conditions, isomerization of the intermediates occurs, while, in th