Tetrapropylammonium Perruthenate, Pr4N+RuO4 -, TPAP: A Catalytic Oxidant for Organic Synthesis

Abstract

This article reviews the oxidations of a wide range of molecules with tetrapropylammonium perruthenate including examples of both double oxidations and selective oxidations. Mechanistic studies are discussed and general experimental procedures are reported. In addition several interesting developments in the chemistry of this reagent are outlined, that is, heteroatom oxidation, cleavage reactions and also its use in sequential reaction processes. In order to present a complete picture examples of failed reactions have been included. 1. Introduction 1.1. Oxoruthenates 1.2. Mechanistic Studies on [RuO₄]^- as an Oxidant 1.3. Experimental Considerations 1.4. Functional Group Compatibility and Selectivity 2. Primary Hydroxyl Group Oxidation 3. Secondary Hydroxyl Group Oxidation 4. Allylic and Benzylic Hydroxyl Group Oxidation 5. Lactol Oxidation 6. Heteroatom Oxidation 7. Cleavage Reactions 8. Tandem or Sequential Reaction Processes 9. Failed Reactions 10. Conclusions