Synthesis and Photochemical Uncaging of Alkene-Protected, Polymer-Bound Vicinal Frustrated Lewis Pairs
Emily A. Latif, Jeremy D. Hilgar, Nathan A. Romero
Abstract
Polymeric materials bearing Frustrated Lewis Pair (FLP) functionality are promising candidates for use as heterogeneous catalysts and adaptive materials, but synthetic access to FLP-functional polymers remains limited due to the incompatibility of FLPs with standard polymerization chemistries. Herein, we describe a synthetic approach that "cages" highly reactive vicinal phosphine-borane FLPs as covalent alkene adducts, which are stable to Ni-mediated vinyl addition polymerization. We discovered that the caged FLP adducts can be photochemically activated to liberate vicinal FLPs, enabling spatiotemporally controlled release of FLPs from polymeric precursors.
Topics & Concepts
ChemistryFrustrated Lewis pairVicinalAlkeneBoraneCovalent bondAdductPolymerizationPolymer chemistryReactive intermediatePolymerPhotochemistryCombinatorial chemistryLewis acids and basesCatalysisOrganic chemistryOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods