7534-41-0Relevant academic research and scientific papers
A simple and efficient procedure for the synthesis of ketone di-sec-alkyl acetals
Ono, Fumiaki,Takenaka, Hirotaka,Eguchi, Yuko,Endo, Masato,Sato, Tsuneo
experimental part, p. 487 - 489 (2009/09/08)
Ketone di-sec-alkyl acetals are obtained in good to excellent yields by treatment of ketones with tri-sec-alkyl orthoformate and the corresponding alcohol in the presence of a catalytic amount of cerium(III) trifluoromethanesulfonate. Georg Thieme Verlag
Oxygen and base-free oxidative heck reactions of arylboronic acids with olefins
Ruan, Jiwu,Li, Xinming,Saidi, Ourida,Xiao, Jianliang
, p. 2424 - 2425 (2008/09/18)
A mild and efficient protocol for palladium-catalyzed oxidative Heck reactions of arylboronic acids with both electron-rich and -deficient olefins is described. In contrast to the normal oxidative Heck coupling, this new method works in the absence of a base, oxygen, or other external oxidants. With a wide variety of substrates tolerated, the method broadens the scope of palladium-catalyzed coupling reactions. Copyright
Hydrogen-bond-directed catalysis: Faster, regioselective and cleaner heck arylation of electron-rich olefins in alcohols
Hyder, Zeynab,Ruan, Jiwu,Xiao, Jianliang
experimental part, p. 5555 - 5566 (2009/06/17)
A general method for the regioselective Heck reaction of electronrich olefins is presented. Fast, highly regioselective Pd-catalysed α-arylation of electron-rich olefins, vinyl ethers (1a-d), hydroxyl vinyl ethers (1e,f), enamides (1g,h) and a substituted vinyl ether (1i) has been accomplished with a diverse range of aryl bromides (2a-r), for the first time, in cheap, green and easily available alcohols with no need for any halide scavengers or salt additives. The reaction proceeds with high efficiency, leading exclusively to the a-products, in 2-propanol and particularly in ethylene glycol. In the latter, the arylation can be catalysed at a palladium loading of 0.1 mol% and finish in as short a time as 0.5 h. The remarkable performance of the alcohol solvents in promoting a regiocontrol is attributed to their hydrogen-bond- donating capability, which is believed to facilitate the dissociation of halide anions from PdII, and hence, the generation of a key ionic Pd II-olefin intermediate responsible for the a product. This belief is further strengthened by the study of a benchmark arylation reaction in 21 different solvents. The study revealed that exclusive α-regioselective arylation takes place in almost all of the protic solvents, and there is a rough correlation between the α-arylation rates and the solvent parameter ETN. The method is simpler, cleaner and more general than those established thus far.
