Metal-free regioselective oxidative biaryl coupling leading to head-to-tail bithiophenes: Reactivity switching, a concept based on the iodonium (III) intermediate

K Morimoto, N Yamaoka, C Ogawa, T Nakae…

Index: Kita, Yasuyuki; Morimoto, Koji; Ito, Motoki; Ogawa, Chieko; Goto, Akihiro; Dohi, Toshifumi Journal of the American Chemical Society, 2009 ,  vol. 131,  # 5  p. 1668 - 1669

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Citation Number: 46

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.