Sulfones and sulfonamides are used extensively in the agrochemical and medicinal chemistry industries. On the other hand, their corresponding mono-aza analogues, sulfoximines and sulfonimidamides had seen limited use in these arenas until recently. These motifs have become increasingly popular due to favourable physicochemical properties that these motifs can offer. Indeed, the sulfoximine group has seen success in clinical drug candidates from Bayer and AstraZeneca. The development of more facile synthetic methods for the preparation of these interesting motifs is further accelerating their exploitation.<br/><br/>This poster presents our work in this field to date, developing metal-free methods for the synthesis of sulfoximines and sulfonimidamides. Using ammonium carbamate as a convenient source of ammonia and bisacetoxyiodobenzene as the oxidant, sulfoxides have been shown to be effective precursors to sulfoximines through NH transfer. Further to this, when subjected to similar conditions, sulfides are directly converted to sulfoximines, with NH and O transfer in one-pot, negating the need for a discrete oxidation step. Further work has shown that when sulfenamides are subjected to mild NH and O transfer conditions, the corresponding sulfonimidamides products can be obtained, allowing access to these motifs in just two synthetic steps.

Synthesis of sulfoximines and sulfonimidamides by highly chemoselective NH and O transfer

ACS Fall 2020 Virtual Meeting

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