Pseudocyclic bis-N-heterocycle-stabilized iodanes - synthesis, characterization and applications

Bis-N-heterocycle-stabilized lambda(3)-iodanes (BNHIs) based on azoles are introduced as novel structural motifs in hypervalent iodine chemistry. A performance test in a variety of benchmark reactions including sulfoxidations and phenol dearomatizations revealed a bis-N-bound pyrazole substituted BNHI as the most reactive derivative. Its solid-state structure was characterized via X-ray analysis implying strong intramolecular interactions between the pyrazole nitrogen atoms and the hypervalent iodine centre.

Automated summary

In this study, Bis-N-heterocycle-stabilized lambda(3)-iodanes (BNHIs) based on azoles were introduced as novel structural motifs in hypervalent iodine chemistry. A performance test in various benchmark reactions showed that a bis-N-bound pyrazole substituted BNHI is the most reactive derivative. The solid-state structure of this compound was characterized through X-ray analysis, revealing strong intramolecular interactions between the pyrazole nitrogen atoms and the hypervalent iodine center.