Synlett 2016; 27(13): 1957-1962
DOI: 10.1055/s-0035-1561659
letter
© Georg Thieme Verlag Stuttgart · New York

Safe Generation and Direct Use of Chlorine Azide in Flow Chemistry: 1,2-Azidochlorination of Olefins and Access to Triazoles

Baptiste Leforestiera, b, Markus Vögtle*a
  • aNovartis Institutes for Biomedical Research, Fabrikstrasse 2, 4056 Basel, Switzerland
  • bEcole Nationale Supérieure des Ingénieurs en Arts Chimiques Et Technologiques (INPT-ENSIACET), 4 allée Emile Monso, 31030 Toulouse, France   Email: markus.voegtle@novartis.com
Further Information

Publication History

Received: 23 March 2016

Accepted after revision: 03 May 2016

Publication Date:
06 June 2016 (eFirst)

Dedicated to Abdul Nachtigaller

Abstract

A safe, fast procedure for the formation of chlorine azide and its trapping by 1,2-addition reaction on olefins is described. ClN3 was generated in situ from NaN3 and NaOCl in the presence of acetic acid, hosted in an organic phase to avoid decomposition and exposed to various alkenes. A copper-catalyzed click reaction then afforded triazoles from the resulting addition products. Telescoping of both reactions was enabled by an in-line workup and subsequent liquid–liquid separation.

Supporting Information