4131-04-8Relevant academic research and scientific papers
Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction
Vekariya, Rakesh H.,Aubé, Jeffrey
supporting information, p. 3534 - 3537 (2016/08/16)
The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.
Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: Application to the total synthesis of luteolin
O'Keefe, B. Michael,Simmons, Nicholas,Martin, Stephen F.
experimental part, p. 4344 - 4351 (2011/07/29)
A general and mild protocol for achieving the carbonylative cross-coupling of sterically hindered, ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.
Carbonylative cross-coupling of ortho-disubstituted aryl iodides. Convenient synthesis of sterically hindered aryl ketones
Michael O'Keefe,Simmons, Nicholas,Martin, Stephen F.
supporting information; experimental part, p. 5301 - 5304 (2009/06/18)
(Chemical Equation Presented) A mild and general protocol for the carbonylative cross-coupling of sterically hindered ortho-disubstituted aryl iodides is reported. Carbonylative Suzuki-Miyaura couplings of a variety of aryl boronic acids provide an array of substituted biaryl ketones in modest to excellent yield. A carbonylative Negishi coupling that utilizes alkynyl nucleophiles is also described.
2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Useful Acylating Agents of Electron-Rich Aromatic and Heteroaromatic Compounds
Cadamuro, Silvano,Degani, Iacopo,Fochi, Rita,Gatti, Antonella,Regondi, Valeria
, p. 311 - 314 (2007/10/02)
2-Substituted 1,3-benzoxathiolium tetrafluoroborates were used for the two-step acylation of electron-rich aromatic and heteroaromatic compounds: 1,3-dimethoxybenzene, 1,3,5-trimethoxybenzene, pyrrole and indoles.In most of the cases intermediate 2,2-disubstituted 1,3-benzoxathioles were obtained in good to high yields (55-100percent) and subsequent hydrolysis of these with mercury(II) oxide and aqueous tetrafluoroboric acid (35percent) in tetrahydrofuran afforded the corresponding ketones in almost quantitative yields.
