24490-31-1Relevant academic research and scientific papers
Synthesis of 2-acylphenol and flavene derivatives from the ruthenium-catalyzed oxidative c-h acylation of phenols with aldehydes
Lee, Hanbin,Yi, Chae S.
supporting information, p. 1899 - 1904 (2015/03/18)
The cationic ruthenium hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- has been found to be an effective catalyst for the oxidative C-H coupling reaction of phenols with aldehydes to give 2-acylphenol compounds. The coupling of phenols with α,β-unsaturated aldehydes selectively gives the flavene derivatives. The catalytic method mediates direct oxidative C-H coupling of phenol and aldehyde substrates without using any metal oxidants or forming wasteful byproducts. A cationic ruthenium hydride complex catalyzes the oxidative C-H coupling of phenols with aldehydes to form 2-acylphenol and flavene derivatives.
Pd-catalyzed sequential C-C bond formation and cleavage: Evidence for an unexpected generation of arylpalladium(II) species
Youn, So Won,Kim, Byung Seok,Jagdale, Arun R.
supporting information; experimental part, p. 11308 - 11311 (2012/08/28)
A Pd(II)-catalyzed reaction engaging alkenyl β-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven β-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.
Solvent affected facile synthesis of hydroxynaphthyl ketones: Lewis acids promoted Friedel-Crafts and demethylation reaction
Li, Wan-Mei,Lai, Hu-Qin,Ge, Zhong-Hua,Ding, Cheng-Rong,Zhou, Ying
, p. 1595 - 1601 (2008/02/01)
Hydroxynaphthyl ketones were obtained with high yields under very mild conditions in the presence of AlCl3 via Friedel-Crafts acylation and demethylation from naphthyl ethers. Several Lewis acids were tested, and AlCl3 was the most efficient catalyst. Copyright Taylor & Francis Group, LLC.
The Catalytic Fries Rearrangement and o-Acylation Reactions Using Group 3 and 4 Metal Triflates as Catalysts
Kobayashi, Shue,Moriwaki, Mitsuhiro,Hachiya, Iwao
, p. 267 - 273 (2007/10/03)
Group 3 and 4 metal triflates (Sc(OTf)3, TiCl(OTf)3, Zr(OTf)4, and Hf(OTf)4) were found to be efficient catalysts in the Fries rearrangement of phenyl or 1 -naphthyl acylates. It was also found that the o-acylation (direct acylation) reactions of phenols and 1-naphthols with acid chlorides proceeded smoothly in the presence of the triflates. Both reactions were successfully carried out using small amounts of the triflates (catalytically), and comparison of catalytic activities of these metal triflates in these reactions is discussed.
Catalytic direct C-acylation of phenol and naphthol derivatives using carboxylic acids as acylating reagents
Kobayashi, Shu,Moriwaki, Mitsuhiro,Hachiya, Iwao
, p. 4183 - 4186 (2007/10/03)
Direct regioselective C-acylation of phenol and naphthol derivatives was carried out by using carboxylic acids as acylating reagents. The reactions proceeded smoothly in the presence of a catalytic amount of Hf(OTf)4 to afford the corresponding aromatic ketones in good yields.
Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis
Kobayashi,Hashiya,Ishitani,Moriwaki,Nagayama
, p. 193 - 202 (2007/10/03)
Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.
The Catalytic Fries Rearrangement of Acyloxy Naphthalenes using Scandium Trifluoromethanesulfonate as a Castalyst
Kobayashi, Shu,Moriwaki, Mitsuhiro,Hachiya, Iwao
, p. 1527 - 1528 (2007/10/02)
The catalytic Fries rearrangement of acyloxy naphthalenes proceeds smoothly using a small amount of scandium trifluoromethanesulfonate (5 molpercent) to afford the corresponding hydroxynaphthyl ketones in high yields.
REACTION OF SINGLET OXYGEN WITH ENOLIC TAUTOMERS OF β-DICARBONYLS. α-HYDROXYLATION OF 2-ACYL- AND 2-CARBOALKOXY-3,4-DIHYDRONAPHTHALEN-1(2H)-ONES
Yoshioka, Michikazu,Nishioka, Takashi,Hasegawa, Tadashi
, p. 1471 - 1474 (2007/10/02)
Dye-sensitized photooxidation of enolic tautomers of naphthalenones (5) gave hydroperoxynaphthalenones (6) and naphthols (7).Deoxygenation of 6 by triphenylphosphine gave hydroxynaphthalenones (8).
