1375415-68-1

Upstream product

• 1483-82-5 phenylethynyl chloride 
• 1133-12-6 N-propyl-toluene-4-sulfonamide 
• 58723-96-9 (Z)-1,2-dichloro-2-phenylethylene 
• 98-59-9 p-toluenesulfonyl chloride 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-74-3 phenylacetylene 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 7436-90-0 2,2-dibromostyrene 

Downstream Products

• 1375415-53-4 N-((E)-1-fluoro-2-phenylvinyl)-N-tosylpropan-1-amine 

Relevant academic research and scientific papers

Transition-Metal-Free One-Step Synthesis of Ynamides

A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.

A Robust One-Step Approach to Ynamides

A robust one-step synthetic strategy for ynamide with cheap and easily available stock chemicals vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect to vinyl dichloride as well as electron-deficient amide were observed.

Gold-Catalyzed Intermolecular [4+2] Annulation of 2-Ethynylanilines with Ynamides: An Access to Substituted 2-Aminoquinolines

A gold-catalyzed intermolecular [4+2] annulation of easily accessible 2-ethynylanilines with ynamides offers a highly region-selective, modular, efficient, and atom-economical strategy for the synthesis of substituted 2-aminoquinolines in up to 93% yield. (Figure presented.).

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.

Copper-catalyzed coupling of 1,2-dibromo-1-styrenes with sulfonamides for the preparation of ynamides

Ynamides were prepared through an efficient copper-catalyzed coupling reaction. In the presence of copper iodide, 1,10-phenanthroline, and Cs 2CO3, the coupling reaction of 1,2-dibromo-1-styrenes with sulfonamides proceeded smoothly

Stereoselective hydrofluorination of ynamides: A straightforward synthesis of novel α-fluoroenamides

α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates.

Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes

Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing