Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy

Jean-Luc Renaud (1) , Sylvain Gaillard (1) , Léo Bettoni (1) , Nicolas Joly (1) , Albert Poater (2)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 UdG - Universitat de Girona

Herein, we report a diaminocyclopentadienone ruthenium tricarbonyl complex-catalyzed synthesis of mono- or dialkylated acyl hydrazide compounds using the borrowing hydrogen strategy in the presence of various substituted primary and secondary alcohols as alkylating reagents. Deuterium labeling experiments confirm that the alcohols were the hydride source in this cascade process. Density functional theory (DFT) calculations unveil the origin and the threshold between the mono- and dialkylation.

Domaines: Chimie organique; Catalyse; Matériaux

Jean-Luc Renaud, Sylvain Gaillard, Léo Bettoni, Nicolas Joly, Albert Poater. Phosphine-Free Ruthenium Complex-Catalyzed Synthesis of Mono- or Dialkylated Acyl Hydrazides via the Borrowing Hydrogen Strategy. Journal of Organic Chemistry, In press, J. Org. Chem., 86, ⟨10.1021/acs.joc.1c00654⟩. ⟨hal-03203785⟩