Abstract
Transition metal catalysts have inevitably been used for C(sp2)-C(sp2) bond forming reactions of aryl halides with sp2-carbon nucleophiles. On the other hand, we have recently developed such a kind of reactions with no aid of transition metal catalysis, utilizing single electron transfer (SET) mechanism. Here, a single electron acts as a catalyst to promote the reaction of aryl halides (Ar-X) with arenes, styrenes or aryl Grignard reagents (ArMgBr) to give biaryls, stilbenes or biaryls, respectively. The common intermediates are anion radicals ([Ar-X]•−) of aryl halides and those ([Ar-R]•−) of coupling products. [Ar-X]•−, generated through SET from a base or ArMgBr to Ar-X, reacts directly with ArMgBr, whereas less reactive arenes and styrenes react with Ar•, generated by decomposition of [Ar-X]•−. All the reactions include, in the last step, SET from [Ar-R]•− to Ar-X to give Ar-R and regenerate [Ar-X]•−.
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