Wang Jin-Ping, Liu Tao, Wu Yichen, Wang Peng
State Key Laboratory of Organometallic Chemistry and Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, CAS 345 Lingling Road, Shanghai 200032, P. R. China.
School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou 310024, P. R. China.
J Am Chem Soc. 2025 Jan 8;147(1):69-77. doi: 10.1021/jacs.4c14153. Epub 2024 Dec 18.
Here, we report a novel strategy for the preparation of diverse heterocycles via a Pd-catalyzed migratory 1,1-cycloannulation reaction (MCAR) of alkenes. Starting from readily available alkenyl amines and alkenyl alcohols, this approach allows the formation of a wide range of five- to seven-membered azaheterocycles and oxaheterocycles with high efficiency and good functional group tolerance. The key to the realization of this reaction is the use of 4-iodophenol or 2-iodophenol derivatives where the phenolic hydroxyl group plays a critical role in controlling the direction of migration and the ring-size of the heterocycles through the formation of a quinone methide intermediate.
在此，我们报道了一种通过钯催化烯烃的迁移性1,1-环化反应（MCAR）制备多种杂环化合物的新策略。该方法从易得的烯基胺和烯基醇出发，能够高效且良好地耐受官能团，形成多种五至七元氮杂环和氧杂环。实现该反应的关键在于使用4-碘苯酚或2-碘苯酚衍生物，其中酚羟基通过形成醌甲基化物中间体，在控制迁移方向和杂环的环大小方面起着关键作用。
