Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent

Org Biomol Chem. 2011 Mar 21;9(6):1927-37. doi: 10.1039/c0ob00813c. Epub 2011 Jan 31.

Abstract

Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Amines / chemical synthesis*
  • Azides / chemical synthesis*
  • Imines / chemical synthesis*
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*

Substances

  • Amines
  • Azides
  • Imines
  • Organophosphorus Compounds
  • triphenylphosphine