131190-49-3Relevant academic research and scientific papers
Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System
Zhu, Quan,Luo, Yunsong,Guo, Yongyan,Zhang, Yushun,Tao, Yunhai
, p. 5463 - 5476 (2021/05/05)
A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.
ORGANOTIN HOMOENOLATE EQUIVALENTS - ACCESS TO β-ACYL- AND β-ARYL-PROPIONALDEHYDES THROUGH HETEROSUBSTITUTED ALLYLTINS AND VINYLTINS
Verlhac, Jean-Baptiste,Pereyre, Michel,Quintard, Jean-Paul
, p. 6399 - 6412 (2007/10/02)
Although, α-ethoxycrotyltributyltin can be used as an equivalent of the homoenolate anion CH3-CHCH2CHO in reactions with acyl chlorides, the non-substituted α-ethoxyallyltributyltin could not be employed in this way. γ-Methoxyvinyltins, easily prepared by hydrostannation of propargylic ethers, are successfully employed as synthetic equivalents of the homoenolate anions -CH2CH2CHO and -CH2CH2COCH3 in reactions with acyl chlorides.A silylated γ-methoxyvinyltin, which is both a vinyltin and an allylsilane, reacts with acyl chlorides and aryl bromides as a promising equivalent of the homoenolate anion -CH2CH2CHO and tolerates a wide range of other reactive functional groups.
