Azoiodazinium Salts – Synthesis and Reactivity

Abstract

A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and demonstrate the ring-opening of the heterocycle-bridged iodonium species. For an exclusive set of dicationic imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center.

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

“…Lastly, we synthesized 3f using the standard procedure for iodoliums with more sophisticated benzimidazole-contain-ing diaryliodonium salt, but we only observed a reproducible yield of 8%. The analysis of its solid-state structure showed the desired connectivity [36].…”

Recent progress in alkynylation with hypervalent iodine reagents

“…More recently, the Nachtsheim group developed N-heteroaromatic alkynyl reagents. 49 Scheme 4 Synthesis of TIPS-EBX (4a) from TsO-Bx (7).…”