Triazolopyridines and triazolopyrimidines were synthesized using a modified Mitsunobu reaction starting from acylated 2-hydrazinopyridines and acylated-hydrazinopyrimidines under mild conditions.

A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower th...

Methyl α(and β)-D-3,4-anhydro-tagatofuranosides are important synthetic building blocks as they undergo regioselective ring-opening to afford exclusively products with the D-fructo configuration. Previous attempts prepare these compounds from corresponding methyl D-fructofuranosides under standard Mitsunobu conditions have led an undesired 9:1 mixture of tagato and psico oxiranes. We now report...

Both enantiomers of 15-hexadecanolide, a sex pheromone component of the stink bug (Piezodorus hybneri), were synthesized by using the Yamaguchi or Mitsunobu macrolactonization reaction of (R)-15-hydroxyhexadecanoic acid prepared from ethyl (R)-β-hydroxybutyrate in 5 steps.

alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA, utilizing the redox system of diethyl azodicarboxylate (DEAD)–triphenylphosphine (TPP) (Fig. 1). Without any prerequisite activation of the alcohol, it is a unique alkylation reaction and widely applied to various phases of organic synthesis. However, the reaction has a serious limitation; the acidic hydrogen in HA has to h...

A vast rate increase in the Mitsunobu reaction of phenols with alcohols where either or both are sterically hindered has been achieved by the use of high concentration combined with sonication.

A series of pyridine ether PPAR agonists were synthesized through an ADDP and PS-PPh3 modified Mitsunobu protocol, which eliminated significant by-product formation. This method proved to be versatile, efficient and amenable to parallel synthesis.

Chiral aziridine sulfides and disulfides were synthesized from readily available and inexpensive R-cysteine by a Mitsunobu reaction; their application in the addition of diethylzinc to aldehydes provides secondary alcohols with up to 99% ee and S-configuration.