Chemistry A European Journal [SoPhy]

Abstract:

A copper-mediated coupling reaction between ynamides and diazo-compounds to produce N -allenamides is reported for the first time. This method enables facile and rapid access to terminal N -allenamides by using commercially available TMS-diazomethane with wide functional group compatibility on the nitrogen. Furthermore, the ubiquity of molecules containing a fluorine moiety in medicine, in agricultural, and material science requires the continuous search of new building blocks, including this unique surrogate. The CuI/diazo protocol was successfully applied to the synthesis of fluorine-substituted N -allenamides. DFT calculations provided insights in the mechanism involved.

Reference :

Yongxiang Zheng, Baptiste Moegle, Santanu Ghosh, Anna Perfetto , Davide Luise, Ilaria Ciofin, and Laurence Miesch

Copper-Catalyzed Synthesis of Terminal vs. Fluorine-Substituted N- Allenamides via Addition of Diazo Compounds to Terminal Ynamides.

Chemistry A European Journal, first published: 26 November 2021- DOI: https://doi.org/10.1002/chem.202103598

Contact :

Laurence Miesch, équipe SOPhy, Institut de Chimie (UMR 7177).