State Key Lab of Urban Water Resource and Environment, School of Science, Harbin Institute of Technology, Shenzhen, Guangdong 518055, China.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Org Lett. 2022 Jun 24;24(24):4365-4370. doi: 10.1021/acs.orglett.2c01565. Epub 2022 Jun 10.
The photoinitiated deaminative [3 + 2] annulation reaction of -aminopyridinium salts with alkenes for the synthesis of functionalized γ-lactams is described. This transformation shows good functional group tolerance as well as excellent diastereoselectivity. Preliminary studies suggest that the employed -aminopyridinium salts generate the key amidyl radical intermediates through N-N bond cleavage via a photoinduced single-electron transfer (SET) process. The amidyl radical species would add to the double bond of alkenes, followed by a radical-mediated annulation process, to afford the desired γ-lactams.
本文描述了 -氨基吡啶盐与烯烃的光引发脱氨[3+2]环加成反应，用于合成官能化的γ-内酰胺。这种转化具有良好的官能团耐受性和出色的非对映选择性。初步研究表明，所采用的 -氨基吡啶盐通过光诱导单电子转移（SET）过程通过 N-N 键断裂生成关键的酰基自由基中间体。酰基自由基物种会加成到烯烃的双键上，然后通过自由基介导的环加成反应，得到所需的γ-内酰胺。
