Since the landmark work of Heck, Negishi and Suzuki on Pd-catalyzed crossing coupling reactions, innovative discovery of new reactions forming C-C bonds and constructing functional olefins via nonmetal catalysts remains an imperative area in organic chemistry. Herein, we report a transition-metal-free arylation method of vinyl pinacolboronates with diaryliodonium salts to form C(sp²)-C(sp²) bond and provide trans-arylvinylboronates. The resulting vinylboronates can further react with the remaining aryl iodides (generated from diaryliodonium salts) via Suzuki coupling to afford functional olefins, offering an efficient use of aryliodonium salts. Computational mechanistic studies suggest radical-pair pathway of the diaryliodonium salts promoted by the multi-functional wet carbonate.

自 Heck、Negishi 和 Suzuki 在 Pd 催化的交叉偶联反应方面的里程碑式工作以来，通过非金属催化剂形成 CC 键和构建功能性烯烃的新反应的创新发现仍然是有机化学中必不可少的领域。在此，我们报道了乙烯频哪醇硼酸酯与二芳基碘鎓盐形成 C(sp ² )-C(sp ² ) 键并提供反式芳基乙烯基硼酸酯的无过渡金属芳基化方法。所得的硼酸乙烯酯可以通过铃木偶联与剩余的芳基碘化物（由二芳基碘盐生成）进一步反应，得到功能性烯烃，从而有效利用芳基碘盐。计算机理研究表明，多功能湿碳酸盐促进了二芳基碘盐的自由基对途径。