53379-37-6

Upstream product

• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 479486-96-9 N,N-dimethyl (trimethylsilyl)methanamide 
• 4392-24-9 Cinnamyl bromide 
• 2680-03-7 N,N-Dimethylacrylamide 
• 71-43-2 benzene 
• 2243-53-0 styrylacetic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 5468-77-9 2-bromo-N,N-dimethylethanamide 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Palladium-catalyzed stereoselective synthesis of (E)-β,γ -unsaturated amides

A facile Suzuki type cross-coupling reaction of alkenylborane with 2-bromo-N,N-dimethylacetamide in the presence of a catalytic amount of tricyclohexylphosphine as the ligand has been demonstrated to be a convenient way for the synthesis of (E)-β,γ-unsaturated amides.

Alkenylation of C(sp3)?H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts

α-Vinylation of phosphonates, phosphine oxides, sulfones, sulfonamides, and sulfoxides has been achieved by selective C?H zincation and copper-catalyzed C(sp3)?C(sp2) cross-coupling reaction using vinylphenyliodonium salts. The vinylation transformation proceeds in high efficiency and stereospecificity under mild reaction conditions. This zincative cross-coupling reaction represents a general alkenylation strategy, which is also applicable for α-alkenylation of esters, amides, and nitriles in the synthesis of β,γ-unsaturated carbonyl compounds.

Role of mono-N-protected amino acid ligands in palladium(II)-catalyzed dehydrogenative heck reactions of electron-deficient (hetero)arenes: Experimental and computational studies

We report here that mono-N-protected amino acids (MPAAs), an important environmentally compatible structural motif, enable acceleration of Pd(II)-catalyzed dehydrogenative Heck reactions between pyridines and electron-deficient arenes with simple alkenes, leading to diversely functionalized C3- or meta-selective alkenylated pyridines and benzenes via non-chelate-assisted C-H activation. A comprehensive theoretical study by DFT calculations discloses that the amino scaffold of the MPAA ligand facilely converts to an X-type ligand by an initial N-H activation, resulting in a relatively low activation barrier for the C-H cleavage of pyridine. Then a property reversal of the amino group from X-type to L-type ligand allows the alkene substitution to take place smoothly, while the carboxyl group enables the formation of an intramolecular hydrogen bond, significantly decreasing the activation barrier for the carbopalladation. The results of calculations and the kinetic isotopic effect measurement support a rate-limiting C-H activation by a mechanism involving a concerted metalation/deprotonation pathway, with an endothermicity of 31.0 kcal/mol in the process.

Copper-catalyzed amidation of acids using formamides as the amine source

Copper-catalyzed amidation of acids with formamides or acetamide for the selective synthesis of amides with the aid of 1,4-diazabicyclo[2.2.2]octane as the ligand and tert-butyl hydroperoxide as the oxidant is presented. This method is highly compatible with a wide range of acids, including alkyl acids, aryl acids, α,β-unsaturated acids, and amino acids. A general and direct route for the synthesis of amides is described. The reaction involves the copper-catalyzed amidation of acids, wherein various formamides and an acetamide are used as the amine source. Importantly, this method represents a new strategy for the direct use of acids in the synthesis of amides. DABCO = 1,4-diazabicyclo[2.2.2]octane, TBHP = tert-butyl hydroperoxide. Copyright

Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane

Treatment of allylic and benzylic halides with N,N- dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis- (triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.