171070-82-9

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 693-02-7 hex-1-yne 
• 183312-28-9 1-(2-((trimethylsilyl)ethynyl)-phenyl)hept-2-yn-1-ol 

Downstream Products

• 182920-41-8 1-[3-(Diphenyl-phosphinoyl)-hepta-1,2-dienyl]-2-ethynyl-benzene 

Relevant academic research and scientific papers

Synthesis of Fluorescent Azafluorenones and Derivatives via a Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition

An original and mild synthetic route for the preparation of novel azafluorenones and derivatives via a ruthenium-mediated [2 + 2 + 2] cycloaddition of α,ω-diynes and cyanamides has been developed. This atom-economical catalytic process demonstrated remarkable regioselectivities to access fluorescent azafluorenone derivatives. The photophysical properties of azafluorenone derivatives have been evaluated, and photoluminescence phenomena at solid and liquid states have been highlighted.

Gold-Catalyzed Aromatizations of 3-Ene-5-siloxy-1,6-diynes with Nitrosoarenes to Enable 1,4-N,O-Functionalizations: One-Pot Construction of 4-Hydroxy-3-aminobenzaldehyde Cores

This work describes gold-catalyzed aromatizations of 3-ene-5-siloxy-1,6-diynes with nitrosoarenes to form 4-hydroxy-3-aminobenzaldehyde derivatives, manifesting the use of nitrosoarenes as 1,4-N,O-functionalization sources. Various 3-ene-5-siloxy-1,6-diynes in benzoid and nonbenzoid types are applicable substrates. A series of 18O- and 2H-labeling experiments have been conducted to exclude gold-π-alkyne intermediates. We postulate a mechanism of dual gold catalysis involving initial formation of gold-π-alkynylgold species that activates a 1,5-hydrogen shift to form reactive 1,6-dipoles, thus furnishing intramolecular Michael-type reactions with nitrosonium electrophiles.

Access toward Fluorenone Derivatives through Solvent-Free Ruthenium Trichloride Mediated [2 + 2 + 2] Cycloadditions

An efficient and practical route for the preparation of highly substituted fluorenones and analogues via solvent-free ruthenium trichloride mediated [2 + 2 + 2] cycloaddition of α,-diynes and alkynes has been developed. This green chemistry approach involves a solventless and atom-economical catalytic process to generate densely functionalized fluorenones and related derivatives of high synthetic utility.

Gold-catalyzed Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates

Gold-catalyzed oxidations of 2-ketonyl-1-ethynyl benzenes with N-hydroxyanilines yield 2-aminoindenone derivatives efficiently. Experimental data suggests that this process involves an α-oxo gold carbene intermediate, generated from the attack of N-hydroxyaniline on furylgold carbene intermediate, rather than the typical attack of oxidants on π-alkynes.

A surprising switch from the Myers-Saito cyclization to a novel biradical cyclization in enyne-allenes: Formal diels-alder and ene reactions with high synthetic potential

If there is an aryl substituent on the acetylene terminus of enyne allenes, then its reaction mode may be changed from the Myers-Saito cyclization to a novel C2-C6 cyclization resulting in a net intramolecular Diels-Alder or ene reaction. As a consequence, the thermal cyclization of readily accessible acyclic enyne allenes can be utilized for the synthesis of complex benzofulvene and benzofluorene derivatives. Kinetic results of the C2-C6 cyclization reaction indicate a two-step reaction pathway with a benzofulvene biradical intermediate.