Aarnav
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MITSUNOBU REACTION WITH PRIMARY AMIDES
Can we do MITSUNOBU reaction of a primary aliphatic amide and an alcohol
Ex:n-butylamide
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clearly_not_atara
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The Mitsunobu reaction depends on the triphenylphosphine/diazo complex deprotonating the target nucleophile; I doubt that n-butylamide will be
deprotonated. If you use an amide instead it probably will not attack the alkoxyphosphonium intermediate.
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CuReUS
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according to wiki,for the mitsunobu reaction to work,the nucleophile must have a pKa less than 15.For comparison,the pKa of acetamide is 16.5.
this paper might help you get what you want-https://www.thieme-connect.de/DOI/DOI?10.1055/s-0033-1340142
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Nicodem
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Thread Moved
17-11-2016 at 08:20 |
Aarnav
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Thanks
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