A general method for the N‐alkylation of NH‐sulfoximines and NH‐sulfondiimines has been developed, employing alkyl bromides with KOH in DMSO at room temperature. A variety of previously inaccessible N‐alkylated sulfoximines and sulfondiimines was prepared in good to excellent yields (up to 97%). As an application, the conditions were used to access the biologically active Suloxifen.magnified image
Rhodium-catalyzed direct coupling of benzothioamides with alkenes proceeds smoothly involving ortho-CH bond cleavage. The thioamides also couple with alkynes under similar conditions accompanied by desulfurization and CN bond cleavage to produce indenone derivatives.The direct coupling of aromatic substrates with alkenes and alkynes involving CH bond cleavage provides atom-and stepeconomical routes for synthesizing π-conjugated molecules.
The copper-catalyzed C-N cross-coupling of sulfondiimines with boronic acids has been developed. The reaction proceeds at room temperature in good to excellent yields and provides access to a variety of N,N'-disubstituted sulfondiimines, including N-(hetero)aryl sulfondiimines and the first reported N-alkenylated sulfondiimine.
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