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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)


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Abstract

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.

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Note

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


Key Words

1,2-diazides


ID: J54-Y2015