Metal-Free Regioselective Oxidative Biaryl Coupling Leading to Head-to-Tail Bithiophenes: Reactivity Switching, a Concept Based on the Iodonium(III) Intermediate
Organic Letters2010Vol. 12(17), pp. 3804–3807
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Koji Morimoto, Nobutaka Yamaoka, Chieko Ogawa, Tomofumi Nakae, Hiromichi Fujioka, Toshifumi Dohi, Yasuyuki Kita
Abstract
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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