Chen Shuqing, Liu Ze-Shui, Yang Tao, Hua Yu, Zhou Zhiyu, Cheng Hong-Gang, Zhou Qianghui
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
The Institute for Advanced Studies, Wuhan University, Wuhan, 430072, China.
Angew Chem Int Ed Engl. 2018 Jun 11;57(24):7161-7165. doi: 10.1002/anie.201803865. Epub 2018 May 16.
Reported is a novel palladium(II)-initiated Catellani-type reaction that utilizes widely accessible aryl boronic acids as the substrates instead of aryl halides, thereby greatly expanding the existing scope of this powerful transformation. This borono-Catellani reaction was promoted by cooperative catalysis between Pd(OAc) and the inexpensive 5-norbornene-2-carbonitrile. Practicality is the striking feature of the reaction: it is run open to air at ambient temperature and no phosphine ligand is needed. This mild, chemoselective, and scalable protocol is compatible with a large range of readily available functionalized aryl boronic acids and bromides, as well as terminating olefins (50 examples, 39-97 % yields). Moreover, the orthogonal reactivity between the borono-Catellani and classical Catellani reaction was demonstrated. This work is expected to open new avenues for developing novel Catellani-type reactions.
报道了一种新型钯（II）引发的卡泰拉尼型反应，该反应使用易于获得的芳基硼酸作为底物而非芳基卤化物，从而极大地扩展了这种强大转化反应的现有范围。这种硼基-卡泰拉尼反应由醋酸钯（Pd(OAc)）与廉价的5-降冰片烯-2-腈协同催化促进。该反应的显著特点是实用性强：在室温下可在空气中进行，且无需膦配体。这种温和、化学选择性且可扩展的方法与多种易于获得的官能化芳基硼酸、溴化物以及端烯烃兼容（50个实例，产率39 - 97%）。此外，还证明了硼基-卡泰拉尼反应与经典卡泰拉尼反应之间的正交反应性。这项工作有望为开发新型卡泰拉尼型反应开辟新途径。
