Good evening,
I was wondering if the different Mitsunobu reagents such as DEAD, DIAD or phosphorane derivatives ( such as (cyanomethylene)trimethylphosphorane) can really influence the yield of conversion for a Mitsunobu reaction ?
And if it is the case, how do you choose the more efficient reagent depending on your substrat and /or the nucleophilic functionnal group you would like to introduce ?
Thank you by advance for your answers
The Mitsunobu reaction mechanism is fairly complex. The initial step DEAD with TPP gives betaine intermediate, Once it form, it deprotonate the acid. The same time alcohol it convert to oxophosphonium ion Intermediate. The formation of these two intermediate will combines to give the required product ester. The yeild of the reaction depends on the formation of intermediate as well as the solvent. If you take dry solvent that will helpfull to get constant yeild always.
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