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Sequential double hydrofunctionalizationalization of alkynes is a powerful method to construct useful vicinal compounds. Herein, we report a cobalt-catalyzed sequential hydrosilylation/hydrohydrazidation of alkynes to afford 1,2- N,Si  compounds via ligand relay catalysis. A phenomenon of ligand relay is found that the tridentate anionic  N -ligand (OPAQ) could capture the cobalt ion from bidentate neutral  P -ligand (Xantphos) cobalt complex. This protocol uses three abundant chemical feedstocks, alkynes, silanes, and diazo compounds, and also features operationally simple, mild conditions, low catalyst loading (1 mol%), and excellent functional group tolerance. The 1,2- N,Si  compounds can be easily further derivatized to afford various substituted silane derivatives via  Si-H  functionalization, alcohols via Fleming-Tamao oxidation, free amines and amides via  N-N  bond cleavage and protection. The asymmetric reaction could also be carried out to afford chiral products with up to 86%  ee . The ligand relay has been supported by control experiments and absorption spectra.

Ligand relay catalysis for cobalt-catalyzed sequential hydrosilylation and hydrohydrazidation of terminal alkynes