74973-27-6

Upstream product

• 1733-40-0 crotonanilide 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 62-53-3 aniline 
• 201230-82-2 carbon monoxide 
• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 36293-05-7 2-methyl-2-phenylpropanoyl chloride 
• 17645-30-6 (E)-crotonanilide 
• 591-51-5 phenyllithium 

Downstream Products

• 110486-96-9 Dimethyl-{2-[3-(1-phenyl-ethyl)-quinolin-2-ylsulfanyl]-ethyl}-amine 
• 110486-70-9 2-Chloro-3-(1-phenyl-ethyl)-quinoline 

Relevant academic research and scientific papers

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

Enantioselective Hydroamidation of Enals by Trapping of a Transient Acyl Species

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.

Conjugate addition of RMgX-3MeLi to α,β-unsaturated amides and α,β-unsaturated carboxylic acids

In the presence of 3 equivalents of MeLi, various Grignard reagents reacted with secondary α,β-unsaturated amides and α,β-unsaturated carboxylic acids to give the corresponding Michael adducts in good yields. Copyright

CONJUGATE ADDITION OF ORGANOLITHIUM REAGENTS TO ACRYLANILIDE ANIONS

Phenyllithium, n-butyllithium, and t-butyllithium were found to add to substituted acrylanilide anions to give the 1,4-addition products in fair to good yields.