Remarkable Rate Acceleration of Baylis-Hillman Reaction of Notorious α,β-Unsaturated Aldehydes Catalyzed by Proton Donor
نویسندگان
چکیده
منابع مشابه
Remarkable influence of microwave heating on Morita-baylis-Hillman reaction in PEG-200
BACKGROUND Morita Baylis Hillman (MBH) reaction is used to introduce carbon-carbon or carbon-heteroatom bond in a molecule. The major drawback of this reaction is the relatively low product yield and long reaction time. Though notable changes have been made to improve the reaction rate and yield of MBH adduct by various groups, a reliable synthetic procedure under ambient temperature in presenc...
متن کاملProbing the mechanism of Baylis-Hillman reaction in ionic liquids.
The kinetic data for a Baylis-Hillman reaction in certain ionic liquids possessing ethylsulfate anion [EtSO(4)](-) demonstrate that the rate determining step (RDS) is second order in aldehyde, but first order in acrylate and DABCO. This observation is similar to the one made by McQuade et al., who carried out this reaction in an aprotic polar solvent like DMSO. However, this is in contrast to t...
متن کاملDifferent Reaction Patterns in the Baylis-Hillman Reaction of Aryl Aldehydes with Phenyl Vinyl Ketone, Phenyl Acrylate and Phenyl Thioacrylate
In the Baylis-Hillman reaction of aryl aldehydes with phenyl vinyl ketone we have observed exclusive formation of diadducts 4, and that the yields of diadduct can reach 80% with increasing amounts of phenyl vinyl ketone. On the other hand, for phenyl acrylate and phenyl thioacrylate, only the normal Baylis-Hillman adduct was obtained. The effects of substituents were also examined and a plausib...
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An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor...
متن کاملMorita–Baylis–Hillman reaction of acrylamide with isatin derivatives
The Morita-Baylis-Hillman reaction of acrylamide, as an activated alkene, has seen little development due to its low reactivity. We have developed the reaction using isatin derivatives with acrylamide, DABCO as a promoter and phenol as an additive in acetonitrile. The corresponding aza version with acrylate and acrylonitrile has also been developed resulting in high product yields.
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ژورنال
عنوان ژورنال: Bulletin of the Korean Chemical Society
سال: 2011
ISSN: 0253-2964
DOI: 10.5012/bkcs.2011.32.3.1087