1139-60-2Relevant articles and documents
An efficient Fe2O3/HY catalyst for Friedel-Crafts acylation of m-xylene with benzoyl chloride
Mu, Manman,Chen, Ligong,Liu, Yunlong,Fang, Wangwang,Li, Yang
, p. 36951 - 36958 (2014)
Iron oxide supported on HY zeolite was prepared and exhibited excellent catalytic performance in the acylation of m-xylene with benzoyl chloride. It was characterized by XRD, BET, XPS, NH3-TPD and Py-IR. The obtained results indicated that the catalytic activity of Fe2O3/HY is enhanced with the increase of Lewis acidic sites. Furthermore, the reaction parameters, including load of Fe2O3, temperature, molar ratio and the dose of catalyst, were optimized. Thus the acylation proceeds effectively to afford 2,4-dimethylphenylacetophenone in 94.1% yield under optimum conditions. Finally, the catalyst was examined for the acylations of a series of arenes, all of the alkyl substituted benzenes were transformed to the corresponding products in satisfactory yields while the acylation of chlorobenzene was sluggish. The catalyst was easily separated from the reaction mixture and reused for five runs without appreciable loss of catalytic activity. the Partner Organisations 2014.
Fischer et al.
, p. 4208 (1961)
Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
, p. 7976 - 7981 (2019/10/10)
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols
Verheyen, Thomas,Van Turnhout, Lars,Vandavasi, Jaya Kishore,Isbrandt, Eric S.,De Borggraeve, Wim M.,Newman, Stephen G.
supporting information, p. 6869 - 6874 (2019/05/10)
An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.
Palladium-Catalyzed Ligand-Free Decarboxylative Coupling of α- Oxocarboxylic Acid with Aryl Diazonium Tetrafluoroborate: An Access to Unsymmetrical Diaryl Ketones
Panja, Subir,Maity, Pintu,Ranu, Brindaban C.
, p. 12609 - 12618 (2018/10/20)
Diaryl ketones are of much importance in organic synthesis as versatile intermediates and in industry for their useful properties. A mild and efficient palladium-catalyzed traditional ligand-free decarboxylative coupling of aryl α-keto carboxylic acid with aryl diazonium fluoroborate has been developed. A series of unsymmetrical diaryl ketones has been synthesized in moderate to good yields using this procedure. A radical pathway involving the acyl radical has been suggested.
