Catalytic Oxidations in Organic Synthesis

Abstract

Abstract Despite the availability of attractive catalytic alternatives the average synthetic organic chemist still clings to the use of expensive, environmentally unacceptable stoichiometric oxidants when confronted with an oxidative transformation. The scope and versatility of alternative catalytic oxygen transfer reagents, which employ a metal catalyst in conjunction with a cheap, readily available oxygen donor, such as hydrogen peroxide, an alkyl hydroperoxide or hypochlorite, are reviewed. These reagents are environmentally more acceptable than their stoichiometric counterparts and eminently suitable for industrial applications. In choosing examples to illustrate the general theme emphasis has been placed on reactions often encountered in organic synthesis, e.g. alcohol oxidations, and those exhibiting unusual chemo‐, regio‐ and stereoselectivities. Both synthetic and mechanistic aspects are discussed. The mechanisms and potential synthetic utility of biomimetic oxygen transfer processes are also reviewed.