Fluorous DEAD

Several fluorous counterparts of common reagents have been reported and many of these are also commercially available. Of some interest is the development of fluorous Mitsunobu reagents. A first generation fluorous DEAD reagent was found to have poor reactivity when difficult Mitsunobu reactions were encountered it has since been replaced with two enhanced, second-generation reagents, (1) and (2), for use in parallel or sequential fluorous chromatography and rapid F-SPE isolation, respectively. 

Fluorous DEAD was prepared and used in a Mitsunobu reaction.Fluorous triaryl phosphine was used for a Wittig reaction.Fluorous boronates were prepared and used in functional transformations and a Suzuki-Miyaura coupling reaction. 

Scheme 3.23 The Mitsunobu reaction with fluorous condensation reagents [24] enables the simple purification of the reaction product and recycling of the reagents TPP (49) and DEAD (52). ( TPP = fluorous triphenylphosphine TPPO = fluorous triphenylphosphine oxide DEAD = fluorous diethyl diazodicarboxylate DCEH = fluorous dicarboxyethoxyhydrazine).

The nickel complex 11, with a fluorous Schiff base as ligand, was prepared from salicylaldehyde and 4-perfluorodecylaniline (Scheme 15). This fluorous Ni complex was used as a catalyst for the conjugate addition of -diketones to diethyl azodicarboxylate (DEAD). The mixture was stirred at 60 C in a mixture of... 

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