96013-66-0Relevant academic research and scientific papers
Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction
Cherney, Emily C.,Engle, Keary M.,Gurak, John A.,Joe, Candice L.,Vasquez, Alena M.
supporting information, p. 10477 - 10484 (2020/08/07)
The palladium-catalyzed, α-selective hydroarylation of acrylates and acrylamides is reported. Under optimized conditions, this method is highly tolerant of a wide range of substrates including those with base sensitive functional groups and/or multiple enolizable carbonyl groups. A detailed mechanistic study was undertaken, and the high selectivity of this transformation was shown to be enabled by the formation of a [PdII(Ar)(H)] intermediate, which performs selective hydride insertion into the β-position of α,β-unsaturated carbonyl compounds.
Enantioselective Hydroamidation of Enals by Trapping of a Transient Acyl Species
Yuan, Pengfei,Chen, Jiean,Zhao, Jing,Huang, Yong
supporting information, p. 8503 - 8507 (2018/07/14)
An enantioselective synthesis of β-chiral amides through asymmetric and redox-neutral hydroamidation of enals is reported. In this reaction, a chiral N-heterocyclic carbene (NHC) catalyst reacts with enals to generate the homoenolate intermediate. Upon highly enantioselective β-protonation through proton-shuttle catalysis, the resulting azolium intermediate reacts with imidazole to yield the key β-chiral acyl species. This transient intermediate provides access to diversified β-chiral carbonyl derivatives, such as amides, hydrazides, acids, esters, and thioesters. In particular, β-chiral amides can be prepared in excellent yield and ee (40 chiral amides, up to 95 % yield and 99 % ee). This modular strategy overcomes the challenge of disruption of the highly selective proton-shuttling process by basic amines.
Rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes: Effective conversion of amines and anilines into amides
Wu, Zhao,Hull, Kami L.
, p. 969 - 975 (2016/02/05)
The rhodium-catalyzed oxidative amidation of allylic alcohols and aldehydes is reported. In situ generated [(BINAP)Rh]BF4 catalyzes the one-pot isomerization/oxidative amidation of allylic alcohols or direct amidation of aldehydes using acetone or styrene as the hydrogen acceptor. The conditions are general, affording good to excellent yields with a wide array of amine and aniline nucleophiles, and chemoselective, other alcohols do not participate in the oxidation reaction. Utilization of biphasic conditions is critical, as they promote an equilibrium between the imine/enamine byproducts and the hemiaminal, which can undergo oxidation to the amide.
CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO N-TOSYLATED α, β-UNSATURATED AMIDES
Nagashima, Hideo,Ozaki, Nobuyasu,Washiyama, Masayoshi,Itoh, Kenji
, p. 657 - 660 (2007/10/02)
N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.).Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure.The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.
