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Topic: DMF as hydride donor  (Read 3411 times)

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Offline kukurbituril

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DMF as hydride donor
« on: July 05, 2011, 10:13:19 AM »
Hello, here is the question: can DMF act as a hydride donor? If it is so, could you post some reference??

Offline mickelcorleone

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Re: DMF as hydride donor
« Reply #1 on: July 05, 2011, 01:10:44 PM »
I think that NO :-\


Offline Honclbrif

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Re: DMF as hydride donor
« Reply #2 on: July 05, 2011, 03:25:37 PM »
Can't say I've ever heard of DMF acting as a hydride donor, but formic acid can. What type of functional group are you trying to reduce?
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Offline kukurbituril

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Re: DMF as hydride donor
« Reply #3 on: July 06, 2011, 03:51:31 PM »
I´ve got a imide group in my molecule and in mass spectra I see the mass of 2 more then my desired product. So one hypothesis was that DMF can somehow act as a reducting agent (reaction is catalysed by palladium) and one carbonyl is reduced to hydroxyl.

Offline Honclbrif

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Re: DMF as hydride donor
« Reply #4 on: July 06, 2011, 04:30:52 PM »
Have you run an IR or NMR on the substrate to confirm the reduction?
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Offline g-bones

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Re: DMF as hydride donor
« Reply #5 on: July 13, 2011, 06:49:37 PM »
If you obtained your mass spectrum via LCMS, the method of ionization is often through protonation.  Typically the eluent is a percentage of formic acid in water and DMF.  This maybe where you get your hyride. 

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