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Upstream product

• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 104464-03-1 1,1-dibromo-2-(2-methylphenyl)ethene 
• 529-20-4 2-methylphenyl aldehyde 
• 72591-20-9 1-bromo-2-(ortho-methylphenyl)ethyne 
• 615-37-2 ortho-methylphenyl iodide 
• 205885-39-8 N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

Metal-Free Hydrophosphoryloxylation of Ynamides: Rapid Access to Enol Phosphates

We herein report a metal-free hydrophosphoryloxylation of ynamides with phosphoric acids, which provides an expeditious route to access useful enol phosphates. The advantages of this protocol include exclusive selectivity, short reaction time, high efficiency, and broad substrate scope. Additionally, the products can serve as good partners in Suzuki-Miyaura cross-coupling.

Br?nsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: Access to oxygen-bridged tetrahydro-1,4-oxazepines

A Br?nsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water is described. This process provides atom-economical access to oxygen-bridged tetrahydro-1,4-oxazepines, where the bridged oxygen atom originates from water. The unique property of the Br?nsted acid shows distinct chemoselectivity from the corresponding gold-catalyzed cycloadditions.

Cationic polycyclization of ynamides: Building up molecular complexity

Polycyclization reactions are among the most efficient synthetic tools for the synthesis of complex, polycyclic molecules in a single operation from simple starting materials. We report in this manuscript a full account on the discovery and development of a novel cationic polycyclization from readily available ynamides. Simple activation of these building blocks under acidic conditions enables the generation of highly reactive activated keteniminium ions, which triggers an unprecedented cationic polycyclization yielding highly substituted polycyclic nitrogen heterocycles possessing up to seven fused cycles and three contiguous stereocenters.

Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles

An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.

Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

Oxadiazolones are first employed as the three-atom coupling partners in the Tf2NH-catalyzed cycloaddition with ynamides. This formal [3 + 2] cycloaddition allows a rapid synthesis of aminoimidazoles with a broad substrate scope. The approach also features a metal-free catalytic cycloaddition process, which may find applications in the synthesis of bioactive molecules. Besides, the resulting N-methyl products can further be readily converted to free N-H aminoimidazoles.

Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: Second-generation approach to potent ureas bioisosteres

(E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.

Keteniminium ion-initiated cascade cationic polycyclization

A novel and efficient keteniminium-initiated cationic polycyclization is reported. This reaction, which only requires triflic acid or bistriflimide as promoters, affords a straightforward entry to polycyclic nitrogen heterocycles possessing up to three co

Copper-free sonogashira cross-coupling of ynamides: Easy access to various substituted ynamides from nonsubstituted ynamides

It is demonstrated herein that palladium-catalyzed Sonogashira cross-coupling of ynamides can be accomplished with moderate to good yields of substituted ynamides in the absence of copper salt, and NaOAc plays an important role in this reaction as an addi