1357012-16-8

Upstream product

• 1197-22-4 N-phenylmethanesulfonamide 
• 50790-29-9 2-benzonitrile 
• 133816-00-9 phenyl(trimethylsilylethynyl)iodonium triflate 
• 75-35-4 1,1-Dichloroethylene 
• 1252671-79-6 1-ethynyl-1,2-benziodoxol-3(1H)-one 
• 62-53-3 aniline 

Downstream Products

• 1333483-22-9 N-phenyl-N-(phenylethylnyl)methanesulfonamide 
• 2243-35-8 2-acetoxyacetophenone 
• 1403981-69-0 (E)-2-(2-(benzylideneamino)phenyl)-N-(methylsulfonyl)-N-phenylacetamide 

Relevant academic research and scientific papers

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Catalyst-Free [4+2] Cycloaddition of Ynamides with 2-Halomethyl Phenols to Construct 2-Amino-4 H-Chromenes and α-Halo Enamides Simultaneously

We report the development of a facile protocol for the [4+2] cycloaddition of ynamides and 2-halomethyl phenols to afford the corresponding 2-amino-4H-chromenes and α-halo enamides under catalyst-free conditions. The reaction proceeds under mild condition

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

Regio- and Stereoselective Hydrophosphorylation of Ynamides: A Facile Approach to (Z)-β-Phosphor-Enamides

The first trans-selective β-hydrophosphorylation of ynamides, which provides a facile approach to (Z)-β-phosphor-enamide derivatives in moderate to excellent yields and with excellent regio- and stereoselectivity, is described. This transition-metal-free reaction is featured with operationally simple procedure, mild reaction conditions, readily available starting materials, broad substrate scope and good functional-group tolerance. It is noted that the (Z)-β-phosphor (V)-enamides can be prepared from the oxidation of the corresponding phosphine derivatives or the direct β-hydrophosphorylation of ynamides with diphenylphosphine oxide. In addition, cis-trans isomerization of (Z)-β-phosphor (V)-enamides can be easily realized to furnish the corresponding (E)-β-phosphor (V)-enamides. This advantageous feature enables the preparation of (Z)-β-phosphor (V)-enamides as well as (E)-β-phosphor (V)-enamides from the same starting materials. (Figure presented.).

Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives

A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted δ-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).

Sulfonamide-directed gold-catalyzed [2+2+2]-cycloadditions of nitriles with two discrete ynamides to construct 2,4-diaminopyridine cores

Gold-catalyzed [2+2+2]-cycloadditions of two discrete ynamides and one nitrile afford 2,4-diaminopyridine derivatives that are not readily prepared from typical low-valent-metal catalysts. Our mechanistic analysis reveals that the reaction chemoselectivit

Synthesis of Oxindoles through the gold-catalyzed oxidation of N-arylynamides

α-Oxo gold carbenoids generated by the oxidation of N-arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N-oxide works as the oxidant, ligand, and base in this transformation. Copyright