I have been synthesizing N-formylated compounds previously using formic acid, but when the formic acid was replaced with deuterated formic acid reaction is not progressing under similar conditions.
I have also tried optimizing reaction at various temperature and time but with no success.
What may be the probable reason for such failure, any suggestions, feedback, links to research publications will be highly appreciated.
Thank you
Maybe you try N-formylation with deuterated Dimethylformamide:
https://pubs.acs.org/doi/full/10.1021/ol201475j?src=recsys#
Possible Reason: Kinetic isotope effec
thttps://ipfs.io/ipfs/QmXoypizjW3WknFiJnKLwHCnL72vedxjQkDDP1mXWo6uco/wiki/Kinetic_isotope_effect.html
I don't think adding one mass unit to formic acid would shut down the reaction completely due to a kinetic isotope effect. For example, we have had no trouble replaceing -CH3 with -CD3 when we methylate an amine. How many equivalents of d-formic acid are you using?
Thank you for your kind suggestions...
I am using 2 equivalent of deuterated formic acid and reaction condition are 80 degree reflux, with no solvent.
I also have a query: what would be the Rf of the deuterated product as compared to non deuterated one in. TLC?
Deuterium affects kinetics of reactions (kinetic isotopic effect), so product formation might just occur slower. You may want to use some coupling reagent, like HBTU or HOBt. It makes coupling milder, hence no deuterium exchange.
There shouldn't be much difference in Rf. Difference in product molecule mass is probably negligible and hydrophobicity should be about same.
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