Sulfones and sulfonamides are used extensively in the agrochemical and medicinal chemistry industries. However, the use of their corresponding mono-aza analogues, sulfoximines and sulfonimidamides, had seen limited use until recently. Their favourable physicochemical properties and opportunities for reaching new IP space make these functionalities attractive moieties to incorporate into new bioactive molecules. The sulfoximine group has seen success in the insecticide sulfoxaflor, developed by Dow AgroSciences and clinical drug candidates from Bayer and AstraZeneca. The recent development of more facile synthetic methods for the preparation of these privileged functional groups is further accelerating their application.<br/><br/>This poster presents our work in this field to date, developing metal-free methods for the synthesis of sulfoximines and sulfonimidamides. With 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. Ongoing work will also be presented on the synthesis of sulfonimidamides from sulfenamides under mild NH and O transfer conditions.

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

2019 Spring National Meeting

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