Synthesis of a triphenylphosphine reagent on non-cross-linked polystyrene support: application to the Staudinger/Aza-wittig reaction

AB Charette; AA Boezio; MK Janes

doi:10.1021/ol006432w

Synthesis of a triphenylphosphine reagent on non-cross-linked polystyrene support: application to the Staudinger/Aza-wittig reaction

Org Lett. 2000 Nov 30;2(24):3777-9. doi: 10.1021/ol006432w.

Authors

AB Charette¹, AA Boezio, MK Janes

Affiliation

¹ Departement de chimie, Universite de Montreal, Quebec, Station Downtown, Canada H3C 3J7.

PMID: 11101417
DOI: 10.1021/ol006432w

Abstract

A new triphenylphosphine reagent linked to a linear polystyrene was synthesized. The reactivity of this phosphine-bound polymer is superior to that of the phosphine bound to cross-linked polystyrene. The polymer reacted very rapidly with azides to generate iminophosphoranes which could then react with aldehydes to generate imines in good yields and high purities.