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Topic: mitsunobu reaction  (Read 2591 times)

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Offline ku85

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mitsunobu reaction
« on: April 19, 2014, 06:22:22 AM »
Hi,

I'm a  newbie here :)
I have a question for you regarding the Mitsunobu reaction
How is the mechanism of the reaction in presence of diphenylphosphoril azide?

thanks for the help

Offline TheUnassuming

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Re: mitsunobu reaction
« Reply #1 on: April 19, 2014, 09:24:36 AM »
Check out the basic mechanism on wikipedia. 
DPPA is simply an N3- source.  The mitsunobu reaction can be done with a fairly diverse set of nucleophiles as long as the pKa of the compound (R group in the wiki article) is in the correct range.  R can be various carboxylates as well as a number of azide/carbamate derivatives. 
When in doubt, avoid the Stille coupling.

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