Catalytic remodeling of complex alkenes to oxonitriles through C=C double bond deconstruction

• 成果类型: Article
• 署名作者: Cheng, Zengrui; Huang, Kaimeng; Wang, Chen; Chen, Lili; Li, Xinyao; Hu, Zhibin; Shan, Xinyuan; Cao, Peng-Fei; Sun, Haofeng; Chen, Wei; Li, Chenhao; Zhang, Ziyao; Tan, Hui; Jiang, Xue; Zhang, Guikai; Zhang, Zhongying; Lin, Min; Wang, Liang; Zheng, Anmin; Xia, Changjiu; Wang, Teng; Song, Song; Shu, Xingtian; Jiao, Ning
• 署名单位: Peking University; Sinopec; Shanghai University; Beijing University of Chemical Technology; Chinese Academy of Sciences; University of Science & Technology of China, CAS; Chinese Academy of Sciences; Innovation Academy for Precision Measurement Science & Technology, CAS; Chinese Academy of Sciences; Institute of High Energy Physics, CAS; University of Chinese Academy of Sciences, CAS; Zhejiang University; Wuhan University of Science & Technology; Changping Laboratory
• 刊物名称: SCIENCE
• ISSN/ISSBN: 0036-12174
• DOI: 10.1126/science.adq8918
• 发表日期: 2025-03-07
• 页码: 1083-1090
• 关键词: natural-products; internal olefins; drug discovery; oxidation; hydroamination; oxygenation; ozonolysis; nitriles; deletion; DESIGN

摘要

Deconstructive transformation of carbon-carbon double bonds (C=C) is a pivotal strategy in synthetic chemistry and drug discovery. Despite the substantial advances in olefin metathesis and ozonolysis for natural product synthesis through C=C double-bond cleavage, the catalytic remodeling of complex molecules through C=C double-bond deconstruction has been underdeveloped. We report a heterogeneous copper-catalyzed C=C double-bond cleavage, which enables the remodeling of complex molecules by converting the carbons on either side of the C=C double bond to carbonyl and cyano groups, respectively. In particular, this method provides an efficient protocol to conveniently transform terpenoids, glycals, steroids, and bioactive molecules to privileged scaffolds with underexplored chemical space.