Aromatic substitution: The treatment of diaryliodonium bromides 1 with aromatic nucleophiles 2, afforded a variety of heteroaryl‐containing biaryls 3 in good yields. The ipso‐substitution process at the heteroaryl ring in 1 occurs through the formation of aromatic cation radicals, which are initiated by the single‐electron‐transfer (SET) oxidation of 2. (HFIP= hexafluoroisopropanol)
A new synthetic concept for obtaining unsymmetrical biaryl coupling products by an oxidative method is reported. Our synthetic strategy casts light on the reaction intermediate for switching the reactivity of 3-substituted thiophenes. On the basis of this strategy, a novel direct method for the synthesis of head-to-tail bithiophenes using hypervalent iodine(III) reagents has been developed.
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