Synthesis of Cyclic and Acyclic ortho-Aryloxy Diaryliodonium Salts for Chemoselective Functionalizations

Two regioselective, high-yielding one-pot routes to oxygen-bridged cyclic diaryliodonium salts and ortho-aryloxy-substituted acyclic diaryliodonium salts are presented. Starting from easily available ortho-iodo diaryl ethers, complete selectivity in formation of either the cyclic or acyclic product could be achieved by varying the reaction conditions. The complimentary reactivities of these novel ortho-oxygenated iodonium salts were demonstrated through a series of chemoselective arylations under metal-catalyzed and metal-free conditions, to deliver a range of novel, ortho-functionalized diaryl ether derivatives.

Automated summary

Two regioselective and high-yielding methods for the synthesis of oxygen-bridged cyclic and ortho-aryloxy-substituted acyclic diaryliodonium salts were presented. These novel compounds exhibited complimentary reactivities in chemoselective arylation reactions, delivering a range of novel ortho-functionalized diaryl ether derivatives.