112126-15-5Relevant academic research and scientific papers
General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols
Parasram, Marvin,Chuentragool, Padon,Wang, Yang,Shi, Yi,Gevorgyan, Vladimir
supporting information, p. 14857 - 14860 (2017/10/31)
A general, efficient, and site-selective visible light-induced Pd-catalyzed remote desaturation of aliphatic alcohols into valuable allylic, homoallylic, and bis-homoallylic alcohols has been developed. This transformation operates via a hybrid Pd-radical mechanism, which synergistically combines the favorable features of radical approaches, such as a facile remote C-H HAT step, with that of transition-metal-catalyzed chemistry (selective β-hydrogen elimination step). This allows achieving superior degrees of regioselectivity and yields in the desaturation of alcohols compared to those obtained by the state-of-the-art desaturation methods. The HAT at unactivated C(sp3)-H sites is enabled by the easily installable/removable Si-auxiliaries. Formation of the key hybrid alkyl Pd-radical intermediates is efficiently induced by visible light from alkyl iodides and Pd(0) complexes. Notably, this method requires no exogenous photosensitizers or external oxidants.
Original syntheses of epoxides involving organoselenium intermediates
Krief,Dumont,Van Ende,Halazy,Labar,Laboureur,Le
, p. 1203 - 1228 (2007/10/02)
β-oxidoalkylselenonium salts and β-oxidoalkylselenones are valuable precursors of a large variety of epoxides. These species were synthesized by reaction of α-selenonio or α-selenonylalkylpotassium with carbonyl compounds or by reaction of a suitable base on β-hydroxyalkylselenonium salts or β-hydroxyalkylselenones, themselves obtained from β-hydroxyselenides. The most powerful method, based on the cyclization of β-hydroxyalkylselenonium salts is fully documented.
Original Syntheses of Carbonyl Compounds and gem-Dihalocyclopropanes from β-Hydroxylalkylselenides
Krief,A.,Laboureur, J. L.,Dumont, W.
, p. 1549 - 1552 (2007/10/02)
β-hydroxyalkylselenides possessing two alkyl substituents on the carbon bearing the selenyl moiety react with dihalocarbenes generated from haloforms and thallous ethoxide or under phase transfer catalysis to produce ring enlarged ketones as the sole product in the first case, as the main product in the second.The reaction takes another course when the dihalocarbenes generated from haloforms and tBuOK or from trihalomethylphenylmercury are employed and leads inter alias to dihalocyclopropanes.
STEREOCHEMICAL OUTCOME OF THE REACTION OF SOME α-SELENOALKYLLITHIUMS WITH 4-t-BUTYL CYCLOHEXANONE
Labar, D.,Krief, A.,Norberg, B.,Evrard, G.,Durant, F.
, p. 1083 - 1100 (2007/10/02)
α-selenoalkyllithiums were found to have a high propensity to add to 4-t-butyl cyclohexanone in an equatorial mode.Stereochemical assignments are discussed.
