湿碳酸根促进的乙烯基频哪醇硼酸酯与二芳基碘鎓盐的自由基芳基化反应生成取代烯烃。
Wet carbonate-promoted radical arylation of vinyl pinacolboronates with diaryliodonium salts yields substituted olefins.
作者信息
Wu Chao, Zhao Chongyang, Zhou Jun, Hu Han-Shi, Li Jun, Wu Panpan, Chen Chao
机构信息
Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, and the Graduate School at Shenzhen, Tsinghua University, 100084, Beijing, China.
Department of Chemistry & Key Laboratory of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Tsinghua University, 100084, Beijing, China.
出版信息
Commun Chem. 2020 Jul 22;3(1):92. doi: 10.1038/s42004-020-00343-8.
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(sp)-C(sp) 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.
自从赫克、根岸英一和铃木章在钯催化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碳-碳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一个至关重要的领域。在此，我们报道了一种无过渡金属的方法，即乙烯基频哪醇硼酸酯与二芳基碘鎓盐进行芳基化反应，以形成C(sp)-C(sp)键并提供反式芳基乙烯基硼酸酯。所得的乙烯基硼酸酯可通过铃木偶联进一步与剩余的芳基碘化物（由二芳基碘鎓盐生成）反应，以提供功能性烯烃，从而实现二芳基碘鎓盐的高效利用。计算机理研究表明，多功能湿碳酸盐促进了二芳基碘鎓盐的自由基对途径。
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