Categories: N-S Bond Formation >
Synthesis of sulfonyl azides
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Recent Literature
In situ preparation of sulfonyl chlorides from thiols by oxidation with N-chlorosuccinimide
(NCS), tetrabutylammonium chloride, and water followed by reaction with amine or
sodium azide in the same reaction vessel enables a convenient synthesis of
sulfonamides and sulfonyl azides.
H. Veisi, R. Ghorbani-Vaghei, S. Hemmati, J. Mahmoodi, Synlett, 2011,
2315-2320.
Lewis base activation enables an opperationally simple protocol for the
efficient conversion of sulfonyl fluorides into sulfonyl azides. The in situ
generated sulfonyl azides are efficient diazo-transfer agents, affording primary
azides and diazo compounds in excellent yields.
A. S. Barrow, J. E. Moses,
Synlett, 2016, 27, 1840-1843.
Related
Triflyl azide serves as an efficient diazo transfer reagent in a direct
synthesis of sulfonyl azide building blocks from readily available and stable
sulfonamides. The process is experimentally simple, mild, and high-yielding.
J. Raushel, S. M. Pitram, V. V. Fokin, Org. Lett.,
2008, 10, 3385-3388.