Mitsunobu Reaction

Schematic representation of the Mitsunobu Reaction.

Mechanism of the Mitsunobu Reaction

Mechanism of the Mitsunobu Reaction

Original publication	Bull. Chem. Soc. Jpn. 1967, 40, 2380. Tetrahedron Lett.. 1999, 40, 2685.
Reviews	Chem. Rev.. 2009, 109, 2551. Org. Prep. Proced. Int.. 1996, 28, 127. Org. React.. 1983, 29, 1. Org. React.. 1992, 42, 335. Synthesis. 1981, 0, 1.

Sample reactions

intermediate structure

(PhO)2P(O)N3, DEAD, Ph3P

THF

0 °C, 24 h, 95%

intermediate structure

intermediate structure

DIAD, Ph3P, Zn(N3)2.2Pyr

THF

RT, 38 h, 30%

intermediate structure

intermediate structure

DEAD, Ph3P, Zn(N3)2.2Pyr

RT, 12 h, 100%

intermediate structure

intermediate structure

DEAD, Ph3P, TsNHBoc

THF

0 °C to RT, 24 h, 88%

intermediate structure

intermediate structure

DIAD, Ph3P

THF

91%

intermediate structure

intermediate structure

(PhO)2P(O)N3, DEAD, Ph3P

THF

0 °C to RT, 40 min, 82%

intermediate structure

intermediate structure

DIAD, Ph3P

THF

RT to Reflux, 3 h

intermediate structure

intermediate structure

intermediate structure

DIAD, Ph3P

THF

0 °C to RT, 2.5 h, 94%

intermediate structure

intermediate structure

DIAD, Ph3P

Et2O

-20 °C, 5 h

intermediate structure

intermediate structure

intermediate structure

n-Bu3P, DEAD

THF

0 °C, 4 h, 83%

intermediate structure

intermediate structure

n-Bu3P, PhSO2NHMe

81%

intermediate structure

intermediate structure

DEAD, Ph3P, 4-Methoxyphenol

CH2Cl2

0 °C to RT, 3 d, 95%

intermediate structure

intermediate structure

intermediate structure

DEAD, Ph3P

PhH

5 °C to RT, 15 min, 90%

intermediate structure

intermediate structure

intermediate structure

DEAD, Ph3P

PhH

5 °C to RT, 15 min, 100%

intermediate structure

intermediate structure

DEAD, Ph3P, ZnBr2

THF

RT, , 91%

intermediate structure

intermediate structure

DEAD, Ph3P, BzOH

Et2O

-25 °C, 60 min

intermediate structure

intermediate structure

DEAD, H2O, LiOH, Ph3P, p-NO2BzOH

THF

-20 °C, 3 h, 80%

intermediate structure

intermediate structure

DEAD, Ph3P

THF

-20 °C, 75 min, 66%

intermediate structure

intermediate structure

DEAD, Ph3P, NsNH2

PhMe

RT, 5 min, 95%

intermediate structure

intermediate structure

(PhO)2P(O)N3, DEAD, Ph3P

THF

50%

intermediate structure

intermediate structure

(PhO)2P(O)N3, DEAD, Ph3P

THF

0 °C, , 88%

intermediate structure

intermediate structure

DEAD, Phthalimide, Ph2PMe

THF

0 °C to RT, 60 min, 50%

intermediate structure

intermediate structure

intermediate structure

DIAD, Ph3P

78%

intermediate structure

intermediate structure

intermediate structure

DIAD, Ph3P

THF

80 °C, 3 h, 54%

intermediate structure

intermediate structure

DIAD, Ph3P

PhH

RT, ON, 98%

intermediate structure

intermediate structure

DEAD, Ph3P, BzOH

PhH

RT, 3 h, 62%

intermediate structure

intermediate structure

DEAD, Ph3P, BzOH

THF

RT, 3 h

intermediate structure

intermediate structure

DIAD, Ph3P, TMS(CH2)2OH

THF

0 °C to RT, 3.5 h, 85%

intermediate structure

intermediate structure

(PhO)2P(O)N3, DEAD, Ph3P

THF

0 °C, 2 h, 82%

intermediate structure

intermediate structure

n-Bu3P, DEAD

4A MS

THF

-15 °C to RT, ON, 30%

intermediate structure