76973-09-6Relevant articles and documents
Kinetics and mechanism of ketone enolization mediated by magnesium bis(hexamethyldisilazide)
He, Xuyang,Morris, J. Jacob,Noll, Bruce C.,Brown, Seth N.,Henderson, Kenneth W.
, p. 13599 - 13610 (2006)
Magnesium bis(hexamethyldisilazide), Mg(HMDS)2, reacts with substoichiometric amounts of propiophenone in toluene solution at ambient temperature to form a 74:26 mixture of the enolates (E)- and (Z)-[(HMDS) 2Mg2(μ-HMDS){μ-
Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source
Xia, Aiyou,Xie, Xin,Hu, Xiaoping,Xu, Wei,Liu, Yuanhong
, p. 13841 - 13857 (2019/10/17)
The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.
Palladium-catalyzed dehydrogenative β-arylation of simple saturated carbonyls by aryl halides
Gandeepan, Parthasarathy,Rajamalli,Cheng, Chien-Hong
, p. 4485 - 4489 (2015/01/09)
(Chemical Equation Presented) A versatile palladium-catalyzed synthesis of highly substituted α,β-unsaturated carbonyl compounds has been developed. In contrast to the known Heck-type coupling reaction of unsaturated carbonyl compounds with aryl halides, the present methodology allows the use of stable and readily available saturated carbonyl compounds as the alkene source. In addition, the reaction proceeds well with low catalyst loadings and does not require any expensive metal oxidants or ligands. A variety of saturated aldehydes, ketones, and esters are compatible for the reaction with aryl halides under the developed reaction conditions to afford α,β-unsaturated carbonyl compounds in good to excellent yields. A possible reaction mechanism involves a palladium-catalyzed dehydrogenation followed by Heck-type cross couplings.