Copper-Catalyzed Vicinal Oxyazidation and Diazidation of Styrenes under Mild Conditions: Access to Alkyl Azides
Ming-Zhu Lu, Cheng-Qiang Wang and Teck-Peng Loh*
*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Email: teckpengntu.edu.sg
M.-Z. Lu, C.-Q. Wang, T.-P. Loh, Org. Lett., 2015, 17, 6110-6113.
DOI: 10.1021/acs.orglett.5b03130 (free Supporting Information)
see article for more reactions
An azidoiodine(III) reagent is used as an efficient azide radical source for efficient copper-catalyzed oxyazidation and diazidation of styrenes in good yields. Various synthetically useful functional groups are tolerated under the mild reaction conditions.
see article for more examples
Azidobenziodoxolone (ABX, Zhdankin reagent) is a valuable azide source, but its safety profile has not been thoroughly established. A safety study of ABX shows its hazardous nature. Two derivatives, tBu-ABX and ABZ (azidobenziodazolone), with a better safety profile are introduced.
S. Alazet, J. Preindl, R. Simonet-Davin,S. Nicolai, A. Nanchen, T. Meyer, Jerome Waser, J. Org. Chem., 2018, 86, 12334-12356. 10.1021/acs.joc.8b02068