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Synthesis of sulfoximines
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In a preparation of N-alkyl-substituted sulfoximines from sulfides, in
situ generated N-bromoalkylamines serve as readily accessible imidating
agents leading to N-alkylsulfiliminium bromides that are subsequently
oxidized providing the desired products. This unprecedented one-pot
imidation/oxidation sequence provides gram quantities of product in a short
period of time avoiding the use of toxic alkylating reagents.
C. A. Dannenberg, V. Bizet, C. Bolm,
Synthesis, 2015, 47, 1951-1959.
The synthesis of N-cyanosulfilimines can readily be achieved by reaction
of the corresponding sulfides with cyanogen amine in the presence of a base and
NBS or I2 as halogenating agents. Oxidation followed by decyanation
affords synthetically useful sulfoximines.
O. García Mancheño, O. Bistri, C. Bolm, Org. Lett., 2007,
9, 3809-3811.