Trimerization of Acetylene and Alkene: Rapid Access to Polyenes

Abstract

Open AccessCCS ChemistryCOMMUNICATIONS22 Dec 2022Trimerization of Acetylene and Alkene: Rapid Access to Polyenes Boxiang Liu, Zhicong Lin, Yu Wang, Tairan Cheng, Tongxiang Cao and Shifa Zhu Boxiang Liu Google Scholar More articles by this author , Zhicong Lin Google Scholar More articles by this author , Yu Wang Google Scholar More articles by this author , Tairan Cheng Google Scholar More articles by this author , Tongxiang Cao Google Scholar More articles by this author and Shifa Zhu Google Scholar More articles by this author https://doi.org/10.31635/ccschem.022.202202579 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Conjugated polyene motifs are ubiquitous in various natural products and functional molecules, however their synthesis is very challenging because of the required lengthy and time-consuming processes. We herein report an efficient approach for the synthesis of (E, E)-trienes via cationic rhodium catalysis using acetylene and simple alkenes bearing diverse directing groups as the starting materials. The reaction features high step economy, excellent functional group compatibility and exclusive stereoselectivity. Various directing groups such as carbonyl, sulfone, phosphate, and even hydroxyl and amino are compatible. Furthermore, the triene products allow versatile elaborations, providing rapid and convenient access to several important bioactive molecules, such as Vitamin A, (+)-Roxaticin and other complex polyenes. The mechanistic experiments show that the directing group on the alkene plays a crucial role in the reaction. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentVolume 0Issue jaPage: 1-22Supporting Information Copyright & Permissions© 2022 Chinese Chemical Society Downloaded 84 times PDF downloadLoading ...