I have been trying to perdeuterate an organic compound (c.a. 5-bromoacenaphthylene-1,2-dione, CAS: 26254-35-3) that has 5 hydrogens, two carbonyls, and one bromide. I tried the hydrothermal reaction for this perdeuteration by using D2O as the deuterium source, 5wt% Platinium/C or 5wt% Rhodium/C + 10wt% Palladium/C as catalysts, and 1-8 MM deuterated chloride (DCl) for acidic condition. The temperature was tried between 200oC up to 300oC from 1-5 days. The mass spectrometry (MS) results show that the compound has been deuterated from 1D to 2D.
Meanwhile, another method that I tried was using trifluoromethanesulfonic acid and benzene-d6 under 40-80oC for two days. The MS results seem to be the same as the previous method. The only improvement was the time and temperature but not the amount of deuteriums.
Is there any suggestion for this reaction?
Thank you~
Perdeuterating electron-deficient organic compounds, especially those with functional groups of carbonyls & halides which are sensitive, can be challenging due to limitations in current methods. To improve perdeuteration, lower temperatures, longer reaction times, and alternative catalysts can be explored. Base catalysis, microwave irradiation, weaker acids, polar solvents, transition metal-catalyzed deuteration, directed ortho metalation, stepwise deuteration, and deuterium gas exchange can be used.
Ooof. Perdeutration is challenging, as you are trying to do C-H activation to all the C-H bonds without damaging the rest of the compound. Can you deuterate the starting materials and then make the perdeutero species from that?
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