LAUSR

A new metal-free procedure allowing a Csp 3-N bond formation through coupling of pyridotriazoles and weakly nucleophilic anilines has been developed. This sustainable reaction shows high tolerance towards functional groups (ketones, free alcohols) leading to 2-picolylamines derivatives. The key to our success is the use of a catalytic amount of TBAB and water as a co-solvent leading to the formation of pyridyl-alkylamines derivatives. As this coupling tolerates the presence of Csp 2-Br bond on both partner of the reaction, this allowed us to perform a sequential one-pot reaction between functionalized triazolopyridines and anilines followed by a second coupling with N-tosylhydrazones leading to the formation of Csp 3-N and Csp 2-Csp 2 bonds.