Alkyl phosphines as reagents and catalysts in organic synthesis

Abstract

A literature review of the major stoichiometric uses of tertiary phosphines, with particular emphasis on the relative abilities of trialkylphosphines and triarylphosphines in Wittig, Staudinger, or Mitsunobu reactions, is presented. Pronounced differences in reaction rates and selectivity, product yields and ease of by-product removal are often observed when trialkylphosphines are compared with triarylphosphines as promoters in these types of reactions. Also presented here is a compilation of some useful physical properties for selected trialkylphosphines, their usual methods of preparation and typical uses in organic synthesis. 1. Introduction 2. Wittig Reaction 2.1. Staudinger Reaction 3. Hydroxyl Replacement Reaction 3.1. Mitsunobu Reaction 3.2. Tertiary Phosphines with Organosulfur and Organoselenium Compounds 3.3. Nitro Compounds and Nitriles 3.4. Reactions with Organic Halides 4. Reactions Catalyzed by Trialkylphosphines 5. Michael Reaction 6. Conclusions.