New groups for energy transfer catalysis and the synthesis of sulfur heterocycles

Objective

Sulfonamides are present multiple FDA approved medicines, and their mono-aza variants, sulfonimidamides, are now also appearing regularly in the medicinal chemistry patent literature. However, the cyclic variants of these molecules are only sparsely present in the chemical literature, despite isolated examples demonstrating encouraging bio-activity. A significant contributor to this absence is the lack of appealing synthetic methods. In this proposal we show how photocatalyzed cycloadditions between sulfinylamine reagents and varied unsaturated coupling partners can be used to access functionalised cyclic variants of sulfonamides and sulfonimidamides. The reactions will be promoted using Energy Transfer (EnT) catalysis. Extensions of the chemistry to access the corresponding di-aza variants, sulfondiimidamides, and to the control of stereochemistry at the sulfur centre, will also be explored.