Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt

Abstract

Diaryliodonium(III) salts have been established as powerful halogen-bond donors in recent years. Herein, a new structural motif for this compound class was developed: iodoloisoxazolium salts, bearing a cyclic five-membered iodolium core fused with an isoxazole ring. A derivative of this class was synthesized and investigated in the solid state by X-ray crystallography. Finally, the potential as halogen-bonding activator was benchmarked in solution in the gold-catalyzed cyclization of a propargyl amide.

Keywords

• diaryliodonium
• gold catalysis
• halogen bonding
• hypervalent iodine
• non-covalent interactions