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. 4Reactions Catalyzed by Trialkylphosphines 5Michael Reaction 6Conclusions

Post-polymerisation modification of poly(3-hydroxybutyrate) (PHB) using thiol–ene and phosphine addition

“…27 Further, phosphines can be regarded as potentially interesting reaction partners for crotonates as they participate in Michael-addition reactions and are commonly used as catalysts. 28,29 Galkin and co-workers reported on the functionalisation of unsaturated carboxylic acids using phosphines. [30][31][32][33][34] In particular, Bu 3 P has been described to form an irreversible acid-phosphine adduct.…”

Photoinduced ligand-to-iron charge transfer enabled C(sp3)–H phosphorylation of hydrocarbons

“…2 Organophosphines have also been utilized as efficient auxiliaries, reagents, and catalysts in numerous landmark transformations, including the well-known Wittig, Mitsunobu, and Staudinger reactions. 3 Among the current methods for the synthesis of phosphine compounds, alkyl and aryl phosphines are mainly obtained via cross-coupling reactions between organometallic reagents (Grignard reagents, organolithium, organozinc, etc .) and halogenated phosphines or phosphanes under certain reaction conditions.…”