898771-06-7Relevant academic research and scientific papers
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.
