[JRebelo]

I have two questions.

The first is, considering that H₂, Pd/C does not normally reduce hetero-double bonds, why can it be used to reduce an imine to an amine? (like in a reductive amination)

The second question is similar to the first and it is, considering that sodium cyanoborohydride does not reduce carbon-carbon double bonds, why can it be used to reduce an enamine to an amine (tertiary) ? (again, like in a reductive amination)


For the first the best thing i could come up with was it may have something to do with the imine tautomerizing to the enamine and the hydrogen reducing the C=C but i really dont know. ive searched around to try and find an answer but came up with nothing. anyone have an idea?

thanks