Diaryliodonium as a double σ-hole donor: the dichotomy of thiocyanate halogen bonding provides divergent solid state arylation by diaryliodonium cations

Abstract

The reactivity of [Ar1Ar2I](SCN) toward the solid-state arylation depends on the preorganization of halogen bond (XB)-bound SCN−: N-XB-bound thiocyanates, which, in contrast to N,S-XB-bound, undergoes the extremely rare N-arylation of SCN−.