ABSTRACT
The realization of the first polymer-on-polymer Mitsunobu reaction, in which a polymeric phosphine is used simultaneously with a polymeric azodicarboxylate, is reported. This strategy employs the use of soluble oligomers generated from ring-opening methathesis polymerization. 31P NMR analysis revealed that the two polymers were interacting to generate the Mitsunobu products. Application to several substrates, as well as comparison experiments with other polymeric reagents, is described.
Subject(s)
Chemistry, Organic/methods , Esters/chemical synthesis , Polymers/chemistry , Biological Factors/chemical synthesis , SolutionsABSTRACT
Soluble and insoluble polystyrene-bound triphenylarsine reagents have been prepared from 4-styryldiphenylarsine. The utility of these reagents as ligands for palladium in Suzuki cross-coupling reactions is demonstrated. In these applications, the use of polymeric triphenylarsine simplifies the purification of the coupled product and allows for the ligand to be recycled. Furthermore, the soluble polymeric arsine reagent permits the palladium catalyst to be recovered and reused.
ABSTRACT
We report herein a simple synthesis of 4-styryldiphenylphosphine and the radical copolymerization of it with styrene, both with and without a cross-linker, to directly form cross-linked and non-cross-linked polystyrene supported triphenylphosphine in which the level of phosphine incorporation can be easily and accurately controlled. The utility of these polymers is demonstrated by their use in Mitsunobu and alcohol bromination reactions.
