79457-89-9

Upstream product

• 58085-33-9 α-phenylcinnamoyl chloride 
• 15866-98-5 ammonium salt of N-p-anisylamino dithiocarbamic acid 
• 40339-42-2 4-methoxy-N-[(1Z)-phenylmethylene]aniline 
• 101-97-3 Ethyl 2-phenylethanoate 
• 108-95-2 phenol 
• 104-94-9 4-methoxy-aniline 
• 886-38-4 diphenylcyclopropenone 
• 501-65-5 diphenyl acetylene 
• 91-48-5 (E)-2,3-diphenylpropenoic acid 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides

Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

(1-Alkynyl)dicarbonylcyclopentadienyliron complexes as electron-rich alkynes in organic synthesis: BF3-mediated [2+2] cycloaddition/ring- opening providing (2-alkenyl-1-imino)iron complexes

Strike while the iron is hot! A BF3-mediated formal [2+2] cycloaddition between (1-alkynyl)iron complexes and aromatic aldehyde imines occurs, which is followed by ring-opening of the initially formed azacyclobutenes to yield (2-alkenyl-1-imino)iron complexes (see scheme). The resulting iron complexes undergo deferric substitution reactions with water under oxidative conditions to afford the corresponding cinnamamides with high E selectivity.

β-LACTAM FORMATION VIA ENOLATE ADDITION: AN UNEXPECTED METHYLENATION REACTION

The condensation of ethyl phenylacetate or ethyl β-hydroxybutyrate with Schiff bases in presence of an excess of lithium diisopropylamide or lithium hexamethyldisilazide leads to unsaturated amides instead of the expected β-lactams.

Investigations on 1,3-Thiazines, 17. - About the Reaction of N-monosubstituted Dithiocarbamates with α,β-Unsaturated Carboxylic Acid Chlorides

The reaction of N-monosubstituted dithiocarbamates with α,β-unsaturated carboxylic acid chlorides yields, depending on the nature of the nitrogen substituent of the dithiocarbamate, the substituents of the acid chloride, and the reaction conditions, eithe