PhIO as a Powerful Cyclizing Reagent: Regiospecific [3+2]-Tandem Oxidative Cyclization of Imine toward Cofacially Self-Aggregated Low Molecular Mass Organic Materials

Abstract

The powerful cyclization and tandem oxidation property of environmentally benign PhIO is developed for the first time, which leads to regiospecific [3+2]-tandem oxidative cyclization of imine at room temperature in rapid access to a new class of compounds, 1,2-functionalized 4,5-diarylimidazoles, in excellent yield with synthetic efficiency. Size, shape, and activity of the involved nanoreactors for the green approach built up from various surfactants are investigated. Spontaneous generation of low molecular mass self-aggregated organic materials, their cofacial one-dimensional packing, and interesting photophysical properties are reported.

p-Carboxyl-N-salicylideneanilines: Simple but efficient chromophores for one-dimensional microrods with aggregation-induced emission enhancement (AIEE) characteristics

“…In particular, one-dimensional (1D) microstructured materials are expected to have distinct advantages as building blocks for miniaturized devices [13][14][15][16]. However, synthesis and preparation methods for reported 1D organic materials are usually complicated [17][18][19][20][21]; furthermore, due to the concentration-quenching effect for most organic fluorophores, fluorescence quantum yields of compounds with intensive emission in solution state would become much lower in their aggregate/solid state [22,23].…”

Recent Advances in Iodosobenzene‐Mediated Construction of Heterocyclic Scaffolds: Transition‐Metal‐Free Approaches and Scope

“…They reported another powerful cyclization and tandem oxidation property of environmentally benign PhIO for rapid access to 1,2‐functionalized 4,5‐diarylimidazoles from aldimine, in excellent yield . The aldimine 102 , when treated with PhIO either in organic solvent or in water/surfactant combination, resulted in a highly substituted imidazole 103 (Scheme ).…”

Iodine-based reagents in photoredox-organocatalysis

“…[20][21] Recently, the utilization of hypervalent iodine reagents as organo-photocatalyst is gaining popularity. [30][31][32][33] Still, this research field requires substantial development, however, limited reports are available towards the use of hypervalent iodine reagents (HIRs) 22,[34][35][36][37][38] as photocatalyst. 39 The suitable combination of HIRs and organo-photocatalyst (OPC) using appropriate light energy and solvent can produce desired functional group transformations.…”