37620-43-2

Upstream product

• 21551-47-3 4,4'-Dimethylchalcon 
• 2757-10-0 N-methylcinnamamide 
• 621-82-9 Cinnamic acid 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 3262-89-3 triphenylboroxine 
• 13565-37-2 trans-4,4'-dimethylchalcone 
• 1517-63-1 4-methylphenyl(phenyl)methanol 
• 122-00-9 para-methylacetophenone 
• 100-52-7 benzaldehyde 
• 766-97-2 4-n-methylphenylacetylene 
• 5720-05-8 4-methylphenylboronic acid 
• 4224-96-8 3-phenyl-1-p-tolylprop-2-en-1-one 
• 93021-70-6 1-phenyl-3-(p-tolyl)prop-2-yn-1-ol 
• 109053-73-8 (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 

Relevant academic research and scientific papers

Uncatalyzed conjugate addition of organozinc halides to enones in DME: A combined experimental/computational study on the role of the solvent and the reaction mechanism

Both aryl and alkylzinc halides prepared by direct insertion of zinc into organic halides in the presence of LiCl underwent the conjugate addition reaction to nonenolizable unsaturated ketones in excellent yield, provided that DME was used instead of THF as the solvent. Diffusion NMR measurements highlighted that the species undergo considerable aggregation under the experimental conditions used in the synthetic procedure, but no substantial differences have been found between the two solvents. Density functional theory calculations, prompted by the experimental aggregation study, revealed an unexpected reaction mechanism, where the coordinating capabilities of DME stabilize a transition state involving two organozinc moieties, lowering the activation energy of the reaction with respect to that seen for THF, enough to explain the fast and quantitative reactions observed experimentally and the different behaviors of the two solvents.

Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions

Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.

Asymmetric Conjugate Addition of Organoboron Reagents to Common Enones Using Copper Catalysts

Copper complexes of phosphoramidites efficiently catalyzed asymmetric addition of arylboron reagents to acyclic enones. Importantly, rare 1,4-insertion of arylcopper(I) was identified which led directly to O-bound copper enolates. The new mechanism is fundamentally different from classical oxidative addition/reductive elimination of organocopper(I) on enones.

Silver hexafluoroantimonate-catalyzed direct α-alkylation of unactivated ketones

A practically simple and direct α-alkylation of unactivated ketones using benzylic alcohols has been achieved. The in situ formed acetals are the key for the success of the reaction. The catalyst, silver hexafluoroantimonate(V) (AgSbF6) provide

Triflic acid promoted direct α-alkylation of unactivated ketones using benzylic alcohols via in situ formed acetals

Direct α-alkylation of unactivated ketones using benzylic alcohols as electrophiles has been achieved at room temperature. This reaction takes place via in situ formed acetal using triflic acid and trimethyl orthoformate. It is believed that methyl vinyl

Gold meets rhodium: Tandem one-pot synthesis of β-disubstituted ketones via meyer-schuster rearrangement and asymmetric 1,4-addition

An asymmetric one-pot tandem Au/Rh-catalyzed synthesis of highly enantioenriched β-disubstituted ketones starting from racemic propargyl alcohols is disclosed. The compatibility of the two metal complexes (Au/Rh) and their orthogonal ligand systems (NHC/d

Regio- and diastereoselective conjugate addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds derived from Oppolzer's sultam

Asymmetric conjugate addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds (1) has been achieved with great regioselectivity (>20:1) and good to excellent diastereoselectivity (de up to 98%). The nucleophilicity and stereospecific blockade of the Grignard reagents play a key role in controlling the regioselectivities and diastereoselectivities of the conjugate addition reaction.