Dear Dr's:
I would like to ask about the effect of NaBH4 on a schiff base have an ester group; does the ester affected by NaBH4?
generally if you keep the reaction for a short time less than 3h the ester will not be affected, but prolonged reaction time and heating may reduce the ester. Also if you add some other metal compounds to tune the reactivity of the borohydride
Generally, esters get reduced by NaBH4, both the ester group and the imine group will be reduced.
Generally, Schiff bases are more reactive towards NaBH4, and can be reduced selectively in the presence of the esters. It all depends on your substrate structure and reaction conditions.
the reduction take place in ice bath, the x-ray of reduced schiff base confirm the reduction of imine group only
https://www.degruyter.com/downloadpdf/j/ncrs.ahead-of-print/ncrs-2016-0383/ncrs-2016-0383.pdf
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