Development of rare metal-free synthetic method using new iodine reagents

Abstract

Oxidation is synthetically important as functional group transformation as well as bond-forming method. Hypervalent iodine reagents such as phenyliodine (III) diacetate (PIDA) and phenyliodine (III) bis (trifluoroacetate) (PIFA) are one of the promising reagents for development of environmentally benign oxidations, due to their mild reactivity, low toxicity, safety, ready availability, and easy handling. Our recent challenge to this chemistry is to enhance the synthetic value of the reagents as useful alternative to highly toxic heavy metal oxidants and even rare transition metals, by pioneering a new method for enabling their efficient utilization and development of unique and new reactivities. During this course, we have succeeded in the development of new recyclable reagent 1 and its catalytic utilization, and design of a new chiral reagent 2 and its application to asymmetric oxidations. The summary of these important achievements in hypervalent iodine (III) chemistry is described herein. © 2009 The Pharmaceutical Society of Japan.