Schematic of the Mitsunobu reaction. Reagents: primary or secondary alcohol, acidic compound (H-Nuc), DEAD, PPh3. Product: substitution product. Comments: Substitution with inversion of stereochemistry.

The Mitsunobu reaction is an organic reaction used to convert a primary or secondary alcohol into a variety of compounds using DEAD and triphenylphosphine. Price of Potassium trichloroammineplatinate(II) (R)-2-Chloro-2-fluoroacetic acid Data Sheet The final product depends on the acidic reagent (the conjugate acid of the nucleophile). The mechanism begins with attack of PPh3 on DEAD which forms a zwitterionic intermediate. This intermediate then deprotonates the acidic compound to reveal the anionic nucleophile. The alcohol starting material then binds to the phosphonium ion and the nucleophile performs a SN2 attack to yield the final substitution product with inversion of stereochemistry. The formation of a strong P=O in the by-product drives this reaction forward. [1][2]

Mechanism

Mechanism of the Mitsunobu reaction. SN2 attack with inversion of stereochemistry.

References:

1.
Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935–939.
2.
Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380–2382.