Palladium-Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3-Dienes via C-H Bond Activation: Efficient Access to 3,4-Dihydroisocoumarin and 5,6-Dihydrocoumalins
Palladium-Catalyzed Formal [4+2] Cycloaddition of Benzoic and Acrylic Acids with 1,3-Dienes via C-H Bond Activation: Efficient Access to 3,4-Dihydroisocoumarin and 5,6-Dihydrocoumalins作者机构:State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Center for Excellence in Molecular Synthesis University of Chinese Academy of Sciences Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China
出 版 物:《Chinese Journal of Chemistry》 (中国化学(英文版))
年 卷 期:2018年第36卷第8期
页 面:708-711页
核心收录:
学科分类:081702[工学-化学工艺] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
基 金:We are grateful to the National Natural Science Foundation of China (Nos. 21772218 21421091 XDB20000000) the "Thousand Plan" Youth program State Key Laboratory of Organome-tallic Chemistry Shanghai Institute of Organic Chemistry and the Chinese Academy of Sciences.
主 题:palladium(ll) C-H bond activation 1,3-diene cycloaddition natural product
摘 要:We report a palladium-catalyzed formal intermolecular [4+2] cycloaddition of benzoic and acrylic acids with 1,3-dienes including the stock chemicals 1,3-butadiene and isoprene leading to synthetically useful 3,4-dihydroisocoumarins and 5,6-dihydrocoumalins. Stepwise C-H bond cleavage and annulation are likely involved in the reaction pathway. The synthetic potential of the methodology was demonstrated by two short derivatizations and total synthesis of natural product Clausamine B.