1201-51-0Relevant academic research and scientific papers
Palladium-catalyzed mono-α-arylation of carbonyl-containing compounds with aryl halides using dalphos ligands
Crawford, Sarah M.,Alsabeh, Pamela G.,Stradiotto, Mark
, p. 6042 - 6050,9 (2020/09/02)
We report the extension and optimization of the [Pd(cinnamyl)Cl] 2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides. Aryl methyl ketones, heteroaryl methyl ketones, propiophenones, malonates, and methoxyacetone can be α-arylated under relatively mild conditions and in good yields. We also report the limitations of the ligand/catalyst system towards other classes of carbonyl-containing compounds. We report the application of the [Pd(cinnamyl)Cl]2/DalPhos catalyst system, previously found effective for the mono-α-arylation of acetone, to the mono-α-arylation of a variety of carbonyl-containing compounds with aryl halides and heteroaryl halides.
Ketone homologation to produce α-methoxyketones: Application to conduritol synthesis
Phillipson, Neil,Anson, Michael S.,Montana, John G.,Taylor, Richard J. K.
, p. 2821 - 2829 (2007/10/03)
The scope of Trost's sulfone homologation procedure for the conversion of ketones into their α-methoxylated higher homologues has been dramatically expanded. The use of zirconium (or hafnium) tetrachloride in the hydroxy sulfone rearrangement step gives g
α-Methoxyketone Synthesis via Ketone Homologation: ZrCl4-Mediated Hydroxy Sulfone Rearrangements
Montana, John G.,Phillipson, Neil,Taylor, Richard J. K.
, p. 2289 - 2290 (2007/10/02)
The adducts between ketones and the anion derived from benzene undergo efficient, regioselective rearrangement to give α-methoxyketones when treated with ZrCl4 and HfCl4; this new procedure allows the sulfone-mediated homologation
A UNIQUE 1,2-SHIFT SELECTIVITY IN 2-HYDROXYPROPIOPHENONE DIMETHYLACETALS: GENERATION OF NEW METHODOLOGIES FOR METHYL-2-ARYLPROPANOATES AND 1,2-CARBONYL TRANSPOSITION
Sonawane, H. R.,Nanjundiah, B. S.,Kulkarni, D. G.,Ahuja, Jaimala R.
, p. 7319 - 7324 (2007/10/02)
α-Hydroxydimethylacetals I have been shown to undergo two different rearrangements involving highly selective 1,2-shifts under mild conditions.When treated with Ph3P/CCl4 in the presence of pyridine, I were cleanly transformed via 1,2-aryl shifts into methyl 2-arylpropanoates, an important class of antiinflammatory agents; a pronounced substituent effect has been observed in this rearrangement. On the other hand, treatment of I with catalytic amount of Ph3P/I2 in benzene furnished α-methoxy-α-aryl propan-2-ones in excellent yields and culminated in the development of a new methodology for 1,2-carbonyl transposition.
