183312-28-9Relevant academic research and scientific papers
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
Kale, Balaji S.,Liu, Rai-Shung
, p. 8434 - 8438 (2019/10/16)
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.
Synthesis of Fluorescent Azafluorenones and Derivatives via a Ruthenium-Catalyzed [2 + 2 + 2] Cycloaddition
Ye, Fei,Tran, Christine,Jullien, Ludovic,Le Saux, Thomas,Haddad, Mansour,Michelet, Véronique,Ratovelomanana-Vidal, Virginie
, p. 4950 - 4953 (2018/08/24)
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 Intermolecular Oxidations of 2-Ketonyl-1-ethynyl Benzenes with N-Hydoxyanilines to Yield 2-Aminoindenones via Gold Carbene Intermediates
Mokar, Bhanudas Dattatray,Huple, Deepak B.,Liu, Rai-Shung
, p. 11892 - 11896 (2016/11/16)
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.
Access toward Fluorenone Derivatives through Solvent-Free Ruthenium Trichloride Mediated [2 + 2 + 2] Cycloadditions
Ye, Fei,Haddad, Mansour,Michelet, Véronique,Ratovelomanana-Vidal, Virginie
, p. 5612 - 5615 (2016/11/17)
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.
Steric effects in enyne-allene thermolyses: Switch from the Myers-Saito reaction to the C2-C6-cyclization and DNA strand cleavage
Schmittel, Michael,Kiau, Susanne,Siebert, Torsten,Strittmatter, Marc
, p. 7691 - 7694 (2007/10/03)
The thermal reaction of enyne-allenes 1 with large substituents (tert.-butyl, trimethylsilyl) at the acetylene terminus leads to C2-C6 cyclization products presumably via an intermediate benzofulvene biradical, whereas with a hydrogen substituent the expected Myers-Saito cycloaromatization product is formed. Effective DNA strand scission can be observed when no intramolecular pathway is available.
