26218-50-8

Upstream product

• 7299-58-3 phenylpropiolyl chloride 
• 124-40-3 dimethyl amine 
• 536-74-3 phenylacetylene 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 24378-05-0 methyl phenylethynyl sulfone 
• 68-12-2 N,N-dimethyl-formamide 
• 28995-82-6 ((Z)-1-Iodo-2-methanesulfonyl-vinyl)-benzene 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 637-44-5 phenylpropyolic acid 
• 32833-96-8 N,N-dimethyloxamic acid 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 201230-82-2 carbon monoxide 
• 75-50-3 trimethylamine 

Downstream Products

• 1279110-68-7 C₁₈H₁₇NO₃ 
• 1279110-67-6 C₁₈H₁₇NO₃ 
• 131214-20-5 (2Z)-N,N-dimethyl-3-phenyl-2-propenamide 
• 1360896-26-9 (E)-N,N-dimethyl-3-phenyl-2-(triethoxysilyl)acrylamide 
• 922522-23-4 [TaCl₃(PhCCCONMe₂)(pyridine)2] 
• 129741-70-4 (E)-(trimethylstannyl)(CONMe₂)CC(Ph)(PPh₂) 
• 129741-69-1 (trimethylstannyl)(CONMe₂)CC(Ph)(PPh₂) 

Relevant academic research and scientific papers

Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2

Herewith, we report the enantioselective epoxidation of electron-deficient cis- and trans-α,β-unsaturated amides with the environmentally benign oxidant H2O2. The catalysts - manganese complexes with bis-amino-bis-pyridine and structurally related ligands - exhibit reasonably high efficiency (up to 100 TON) and excellent chemo- and enantioselectivity (up to 100% and 99% ee, respectively). Crucially, the cis-enamides epoxidation enantioselectivity and yield are dramatically enhanced by the presence of NH-moiety, which effect can be explained by the hydrogen bonding interaction between the cis-enamide substrate and the manganese based oxygen transferring species. (Figure presented.).

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l

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

Graphitic Carbon Nitride Polymer as a Recyclable Photoredox Catalyst for Decarboxylative Alkynylation of Carboxylic Acids

Visible-light-induced heterogeneous photocatalysis for decarboxylative alkynylation has been performed. The using of cheap, metal-free and recyclable graphitic carbon nitride (g-C3N4) as the photoredox catalyst in the process enables

Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes

Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.

Metal-Free Transfer Hydroiodination of C-C Multiple Bonds

The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.

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.

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.

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).

A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes

Visible-light-promoted intermolecular radical cyclization of disulfides and alkynes has been developed. Benzothiophenes bearing ester, ketone, aldehyde and aryl substituents were synthesized in good yields. The reaction was carried out in the absence of t