title: Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent.
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.
authors.affiliation: Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK CB2 1EW.
authors.forename: Catherine J
authors.initials: CJ
authors.lastname: Smith
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Smith
authors.forename: Nikzad
authors.initials: N
authors.lastname: Nikbin
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
authors.forename: Ian R
authors.initials: IR
authors.lastname: Baxendale
mesh_terms: D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D001386:Azides; D007097:Imines; D009943:Organophosphorus Compounds; C061896:triphenylphosphine