Iridium-catalyzed N-alkylation of diamines with glycerol

• We report a novel glycerol valorization route which proceeds via iridium-catalyzed dehydrogenation.
• Reaction of glycerol with 1,2-diaminocyclohexanes gives N-heterocyclic products.
• The process is catalyzed by [Cp*IrCl2]2 and K2CO3 in water at 100 °C.
• Evidence for hydrogen-borrowing mechanism is obtained by reaction of the diamine with a glycerol acetal.

N-alkylation of 1,2-diaminocyclohexanes with glycerol in water, catalyzed by [Cp*IrCl2]2, gives a mixture of 2-methyldecahydroquinoxaline and 2-(1-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-benzimidazoles.

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