Synthesis of Alkynamides From Carbamoyl Fluorides Through Metal-Free Fluoride Catalysis

Alkynamides are very promising inhibitors of tyrosine kinases, important enzymes that can cause cancer when being too active in cells due to different mutations. While being important moieties, until recently there was no convenient method to synthesize them using carbamoyl fluorides — most protocols use either dangerous or expensive and ecologically unfriendly reagents, which always have an impact on the final product price and also makes these reactions not suitable to use in large-scale synthesis. This research will expand the application of a recently discovered by our group reaction, which allows us to synthesize corresponding compounds using easy-accessible carbamoyl fluorides and trimethylsilyl-alkynes in the presence of TBAF (tetrabutylammonium fluoride). That makes this reaction atom-economical, easy to handle, relatively cheap, and ecologically friendly.
The success of this project will give us a new powerful tool in organic chemistry, that will provide new convenient ways to synthesize alkynamides. It will also increase their availability to medicinal chemistry, which in turn can have a positive impact on the future development of new anti-cancer drugs.

Faculty Supervisor:

Christine Le

Student:

Partner:

Taras Shevchenko National University of Kyiv

Discipline:

Life Sciences

Sector:

Life Sciences (not health); Pharmaceuticals; Health and Related Sciences & Technology

University:

York University

Program: