Design and synthesis of new electrophilic reagents based on sulfur

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The organic chemistry of hypervalent iodine compounds has experienced an explosive development during the last decade mainly due to their ability to serve as electrophilic transfer reagents for a variety of functionalities such as -CF3, -NR2 and alkynes among others. Their synthesis and use however, requires working under appropriate safety measures due to their potentially explosive nature. Herein, we propose the use of imidazolium sulfuranes and derivatives as alternative platforms for the development of user-friendlier electrophilic group-transfer reagents. We also design plausible synthetic pathways that should lead to their preparation, and suggest several model transformations where their reactivity should be tested. Our preliminary experiments on electrophilic cyanation have already confirmed in this case the validity of our concept.