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

Smith, C. J., Smith, C. D. ORCID: https://orcid.org/0000-0002-5911-5836, Nikbin, N., Ley, S. V. and Baxendale, I. R. (2011) Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent. Organic and Biomolecular Chemistry, 2011 (9). pp. 1927-1937. ISSN 1477-0520 doi: 10.1039/c0ob00813c

Abstract/Summary

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.