SNAr-Functionalization of Diaryliodonium Salts: Access to Densely Substituted Arenes.

Diaryliodonium salts are efficient electrophilic arylation reagents for a wide variety of nucleophiles. The main limitation in the arylation scope is often the difficulty in synthesizing advanced heteroatom-functionalized diaryliodonium salts, due to their sensitivity to acidic and oxidative conditions. We present a general SNAr strategy to functionalize fluoro-substituted iodonium salts, which enables the synthesis of a wide range of heteroatom-functionalized iodonium salts, with demonstrated reactivity in a variety of transition-metal-free O-, N-, and S-arylations to provide densely functionalized aromatic products.