14252-17-6Relevant academic research and scientific papers
Novel bisamide palladium(II) pincer complexes: effective catalysts in α-arylation of ketones
Kai, Wang,Liu, Dabin,Qian, Hua,Ye, Zhiwen
, p. 443 - 450 (2017/07/12)
Three benzenedicarboxamide ligands (L) were designed and synthesized, and each was used to prepare a palladium(II) complex Pd(L)Br and Pd(L)(OAc). These NCN pincer complexes were used to catalyze the α-arylations of a variety of ketones with aryl chlorides or bromides in various solvents, and moderate-to-excellent yields were obtained (up to 95%). Further research showed that unactivated and sterically hindered aryl halides and ketones are also suitable substrates for the synthesis of α-arylation. Graphical Abstract: [Figure not available: see fulltext.].
"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.
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.
