Towards the Synthesis of a Biphenyl Based Water-soluble Hypervalent Iodine Reagent to Probe Hypervalent Iodine Twist.

摘要

Hypervalent iodine twist is a recently identified phenomenon in oxidation of alcohols using o-iodoxy benzoic acid (IBX). Hypervalent twist refers to the movement of ligands in IBX-alcohol adduct formed by ligand exchange. Planarity of oxo-ligands allows transition state to resemble iodosobenzoic acid (IBA). Here we report synthesis of biphenyl precursors for synthesis of a biphenyl based hypervalent iodine reagent requiring hypervalent twist for oxidation to occur. The structural feature of the reagent could either slow down the oxidation of alcohols or accelerate it. The new reagent will also possess hydrophilic groups positioned such that the reagent is water soluble and potentially oxidize alcohols by H- abstraction mechanism. Progress towards synthesis of biphenyl reagent will be discussed.