Generation and Application of Silyl Acyl Radicals: Facile and Metal-Free Access to Acylsilanes

Open AccessCCS ChemistryCOMMUNICATIONS23 Aug 2024Generation and Application of Silyl Acyl Radicals: Facile and Metal-Free Access to Acylsilanes Yuan-Cui Wan, Yan Huang, Yu Shao, Le-Wu Zhan, Ding-Hai Wang, Bin-Dong Li and Jing Hou Yuan-Cui Wan , Yan Huang , Yu Shao , Le-Wu Zhan , Ding-Hai Wang , Bin-Dong Li and Jing Hou Cite this: CCS Chemistry. 2024;0:1–24https://doi.org/10.31635/ccschem.024.202404699 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Acylsilanes are versatile building blocks that are widely used in organic transformations. However, the current synthetic approaches require multiple steps and silyl metals or sensitive reagents or copious amounts of transition-metal catalysts, complex ligands, and elevated temperatures. In this study, a novel visible-lightmediated, metal-free approach for generating silyl acyl radical intermediates via the reaction of silyl radicals and CO is reported. By trapping the species with various reagents, a wide range of acylsilanes could be accessed smoothly under mild conditions with high atom economy. Gram-scale synthesis can be easily achieved using continuous-flow reactors, indicating the potential for industrial-scale manufacturing and enhanced process safety. Furthermore, these generated acylsilanes can be employed in synthesizing valuable skeletons, such as α-alkoxyorganoboronate esters, cyclopropanes, modified tryptophan containing oligopeptides and α-silyl alcohols through simple transformations. We anticipate that this strategy can be broadly applicable for constructing diverse acylsilanes and can complement current catalysis methodologies. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2024 Chinese Chemical Society Downloaded 0 times PDF downloadLoading ...