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DMF as hydride donor
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Topic: DMF as hydride donor (Read 4815 times)
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kukurbituril
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DMF as hydride donor
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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??
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mickelcorleone
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Organic Chemistry(Organic Synthesis)
Re: DMF as hydride donor
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Reply #1 on:
July 05, 2011, 01:10:44 PM »
I think that NO
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Honclbrif
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Re: DMF as hydride donor
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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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kukurbituril
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Re: DMF as hydride donor
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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.
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Honclbrif
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Re: DMF as hydride donor
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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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g-bones
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Re: DMF as hydride donor
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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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DMF as hydride donor