Categories: N-S Bond Formation >
Synthesis of sulfonyl azides
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.
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.