Department of Chemistry, University of Science and Technology of China, Center for Excellence in Molecular Synthesis of CAS, Hefei, Anhui 230026, P. R. China.
School of Chemical and Materials Engineering, Anhui Province Key Laboratory of Low Temperature Co-Fired Materials, Huainan Normal University, Huainan, Anhui 232038, P. R. China.
Org Lett. 2022 Dec 30;24(51):9413-9418. doi: 10.1021/acs.orglett.2c03807. Epub 2022 Dec 19.
Herein, we report a photoinduced TBADT-catalyzed formal all-carbon [3+2] cycloaddition of aromatic aldehydes and arylethynyl silanes, which combines acyl C-H and C-H activation of aromatic aldehydes, offering a new method for constructing the indanone scaffold under mild conditions. By choosing an appropriate silane as the precursor, one can selectively retain or remove the α-silyl group of the indanone products during the reaction. Preliminary mechanistic studies point to a reaction mechanism involving a 1,5-H shift as a key step.
在此，我们报告了一种光诱导的 TBADT 催化的芳基醛和芳基乙炔基硅烷的形式全碳 [3+2] 环加成反应，该反应结合了芳基醛的酰基 C-H 和 C-H 活化，为在温和条件下构建茚满酮骨架提供了一种新方法。通过选择合适的硅烷作为前体，在反应过程中可以选择性地保留或去除茚满酮产物的α-硅基。初步的机理研究表明，该反应涉及 1,5-H 迁移的反应机理是关键步骤。
