649756-96-7Relevant academic research and scientific papers
Arylation of Aldehydes to Directly Form Ketones via Tandem Nickel Catalysis
Lei, Chuanhu,Zhu, Daoyong,Tangcueco, Vicente Iii Tiu,Zhou, Jianrong Steve
supporting information, p. 5817 - 5822 (2019/08/26)
A nickel-catalyzed arylation of both aliphatic and aromatic aldehydes proceeds with air-stable (hetero)arylboronic acids, with an exceptionally wide substrate scope. The neutral condition tolerates acidic hydrogen and sensitive polar groups and also preserves α-stereocenters of some chiral aldehydes. Interestingly, this nickel(0) catalysis does not follow common 1,2-insertion of arylmetal species to aldehydes and β-hydrogen elimination.
"Greener" Friedel-Crafts acylations: A metal- and halogen-free methodology
Wilkinson, Mark C.
supporting information; experimental part, p. 2232 - 2235 (2011/06/24)
Chemical equations presented. The utility of methanesulfonic anhydride for promoting the Friedel-Crafts acylation reaction of aryl and alkyl carboxylic acids is disclosed. This reagent allows the preparation of aryl ketones in good yield with minimal waste containing no metallic or halogenated components, clearly differentiating it from other available methodologies.
Photoenolization of 2-(2-methyl benzoyl) benzoic acid, methyl ester: Effect of e photoenol lifetime on the photochemistry
Konosonoks, Armands,Wright, P. John,Tsao, Meng-Lin,Pika, Jana,Novak, Kevin,Mandel, Sarah M.,Krause Bauer, Jeanette A.,Bohne, Cornelia,Gudmundsdottir, Anna D.
, p. 2763 - 2770 (2007/10/03)
(Chemical Equation Presented) Photolysis of 3 in argon-saturated 2-propanol led to formation of 5 via intermolecular H-atom abstraction followed by lactonization. Irradiation of 4 in 2-propanol gave compounds 6 and 7 that also come from intermolecular H-atom abstraction. In contrast, photolysis of an oxygen-saturated solution of 3 in 2-propanol yields products 8, 9, and 10, which were all formed from intramolecular H-atom abstraction and trapping of the corresponding biradical with oxygen. Laser flash photolysis of 3 in methanol showed formation of biradical 3BR (γmax 330 nm, and τ = 50 ns) via intramolecular H-atom abstraction as the main photoreactivity of 3. Biradical 3BR decayed into photoenols 3Z and 3E (γmax 390 nm, τ= 6.5 μs and τ = 162 μs, respectively). In comparison, laser flash photolysis of 4 yielded photoenols 4Z and 4E (γmax 390 nm, τ = 15 μs and τ = 3.6 ms, respectively). Thus photoenol 3E is unusually short-lived, and therefore it does not undergo the intramolecular lactonization as we have observed for the analogous photoenol 1E. Photoenol 3Z decays back to 3 via an intramolecular 1,5-H shift, whereas photoenol 3E reforms 3 efficiently via the solvent with the aid of the ortho ester group. The intramolecular lactonization of photoenols 1E and 3E must be a slow process, presumably because the photoenols are rigid and the hydroxyl group is inhibited, by intramolecular hydrogen bonding, from acquiring the correct geometry for lactonization. Thus only photoenols that are resistant to reformation of their ketone via the solvent are long-lived enough to undergo lactonization and release the alcohol moiety.
High-Throughput Synthesis of Alkylbenzophenones with Indium Triflate in the Absence of Solvents Using Microwave
Koshima, Hideko,Kubota, Masashi
, p. 3983 - 3988 (2007/10/03)
A series of alkylbenzophenones were rapidly and efficiently prepared from alkylbenzenes and benzoyl chlorides by Friedel-Crafts acylation catalyzed with indium triflate under solvent-free conditions by microwave heating.
