85241-00-5

Upstream product

• 88-10-8 N,N-diethylcarbamyl chloride 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 109-89-7 diethylamine 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 637-44-5 phenylpropyolic acid 
• 2996-92-1 phenyl trimethylsiloxane 
• 51590-64-8 N-diethyl-2-propynamide 
• 1020203-56-8 3-bromo-N,N-diethylpropiolamide 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 121-44-8 triethylamine 
• 25290-18-0 N,N-diethyl-3-hydroxy-3-phenylpropionamide 
• 41658-04-2 N,N-diethyl 3-oxo-3-phenylpropanamide 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 

Downstream Products

• 84039-69-0 (2Z)-N,N-diethyl-3-phenyl-2-propenamide 
• 1264264-29-0 N,N-diethyl-3-phenyl-3-(phenylsulfonyl)acrylamide 
• 1293988-30-3 C₁₉H₂₁NO₃S 
• 80467-87-4 3,3-diphenylpropanoic acid N,N-diethylamide 
• 34906-86-0 N,N-diethyl-2-oxo-2-phenylacetamide 
• 22396-72-1 diethyl-(3-phenyl-prop-2-ynyl)-amine 
• 3977-92-2 cis-2-phenylcyclopropanecarboxylic acid diethylamide 
• 148960-94-5 2,3-dioxo-3-phenyl-propionic acid diethylamide 

Relevant academic research and scientific papers

Selective syntheses of metalated pyridines from two different unsymmetrical acetylenes, a nitrile, and a titanium(II) alkoxide

Cyclotrimerization of two different, unsymmetrical acetylenes and p-toluenesulfonylnitrile with a divalent titanium alkoxide reagent, Ti(O-i-Pr)4/2 i-PrMgCl, yielded single pyridyltitanium compounds in a highly selective manner. These metalated pyridines were confirmed by deuteriolysis to give the corresponding deuterated pyridines and underwent iodinolysis and copper-catalyzed alkylation to demonstrate their synthetic utility. Alternatively, a different type of cyclotrimerization of an alkynamide, terminal acetylenes, and α-alkoxynitriles mediated by the same titanium(II) alkoxide again proceeded in a highly selective manner to give single pyridines having a titanated side chain. Copyright

Synthesis of 2-ynamides by direct palladium-catalyzed oxidative aminocarbonylation of alk-1-ynes

A novel synthesis of 2-ynamides (3) by palladium-catalyzed oxidative aminocarbonylation of alk-1-ynes (1) is reported. Reactions are catalyzed by PdI2/KI and are carried out at 100°C in dioxane as the solvent in the presence of dialkylamines (2) as nucleophiles (amine/alk-1-yne molar ratio=1/1) using a 4/1 CO/air mixture (20 atm total pressure at 25°C).

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

CuCl2-catalyzed highly stereoselective and chemoselective reduction of alkynyl amides into α,β-unsaturated amides using silanes as hydrogen donors

A CuH-catalyzed Z-selective partial reduction of alkynyl amides to afford α,β-unsaturated amides using silane as the hydrogen donor is developed. This reaction is carried out under mild conditions and able to accommodate a broad scope of alkynyl amides in

Palladium-Catalyzed Oxidative C≡C Triple Bond Cleavage of 2-Alkynyl Carbonyl Compounds Toward 1,2-Dicarbonyl Compounds?

A new, general palladium-catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2-alkynyl carbonyl compounds, including 1,3-disubstituted prop-2-yn-1-ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2-dicarbonyl compounds, e.g., 1,2-diones, 2-keto amides and 2-keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.

Method for synthesizing alpha, beta-unsaturated alkyne amide compound through oxidative carbonylation

The invention relates to a method for synthesizing an alpha, beta-unsaturated alkyne amide compound by oxidative carbonylation, which comprises the following steps: by using terminal alkyne and a diamine compound as raw materials, water-soluble alpha-diim

Palladium-catalyzed decarboxylative aminocarbonylation with alkynoic acid and tertiary amine for the synthesis of alkynyl amide

We developed a method for the synthesis of alkynyl amides via the carbonylation of alkynoic acids and C-N activation of tertiary amines. The reaction of alkynoic acid and tertiary amine with carbon monoxide using a palladium catalyst in the presence of oxygen, KI, and K3PO4, gave the desired alkynyl amides in good yields.

N-triflyl-propiolamides: Preparation and transamidation reactions

N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

Borinic Acid Catalysed Reduction of Tertiary Amides with Hydrosilanes: A Mild and Chemoselective Synthesis of Amines

A reduction of various aryl, alkyl, and α,β-unsaturated amides with phenylsilane, catalysed by a borinic acid, is reported. The unprecedented reaction was carried out under very mild conditions and led to useful amines. Furthermore, the reaction tolerates a variety of functional groups. Initial investigations implicated that an intermediate diarylhydroborane is involved in the reaction mechanism.