Diaryliodonium as a double σ-hole donor: the dichotomy of thiocyanate halogen bonding provides divergent solid state arylation by diaryliodonium cations
Natalia S. Soldatova, Павел С. Постников, Vitalii V. Suslonov, Troyana Yu. Kissler, Daniil M. Ivanov, Mekhman S. Yusubov, Bartomeu Galmés, Antonio Frontera, Vadim Yu. Kukushkin
Abstract
The reactivity of [Ar<sup>1</sup>Ar<sup>2</sup>I](SCN) toward the solid-state arylation depends on the preorganization of halogen bond (XB)-bound SCN<sup>−</sup>: <italic>N</italic>-XB-bound thiocyanates, which, in contrast to <italic>N</italic>,<italic>S</italic>-XB-bound, undergoes the extremely rare <italic>N</italic>-arylation of SCN<sup>−</sup>.
Topics & Concepts
ChemistryHalogenThiocyanateHalogen bondSolid-stateReactivity (psychology)CrystallographyStereochemistryInorganic chemistryPhysical chemistryOrganic chemistryAlternative medicineMedicinePathologyAlkylCrystallography and molecular interactionsSulfur-Based Synthesis TechniquesFluorine in Organic Chemistry