Shao Yu, Ying Cheng-Jie, Wan Yuan-Cui, Zhan Le-Wu, Li Bin-Dong, Hou Jing
College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China.
Org Lett. 2024 Oct 11;26(40):8486-8491. doi: 10.1021/acs.orglett.4c02998. Epub 2024 Sep 30.
The development of efficient methods for synthesizing β-silyl amines has long been a significant goal in organic synthesis. Previous methods mainly relied on the use of prefunctionalized substrates or special reagents. Herein, we present a visible-light-promoted synthesis approach for β-silyl amines, utilizing a combination of photoinduced energy and hydrogen atom transfer processes. Using flow chemistry technology, a variety of valuable skeletons, including β-silyl amines and α-amino esters, can be produced from readily available feedstocks such as hydrosilanes and simple alkanes. Moreover, the strategy's full-process fluidized production capability highlights its potential for industrial-scale manufacturing. Mechanistic studies revealed that oxime esters can act as radical precursors as well as hydrogen atom transfer reagents.
长期以来，开发高效合成β-硅基胺的方法一直是有机合成中的一个重要目标。以前的方法主要依赖于使用预官能化的底物或特殊试剂。在此，我们提出了一种可见光促进的β-硅基胺合成方法，该方法利用了光诱导能量转移和氢原子转移过程的结合。使用流动化学技术，可以从硅烷和简单烷烃等易得的原料中制备包括β-硅基胺和α-氨基酯在内的各种有价值的骨架。此外，该策略的全流程流化生产能力突出了其在工业规模制造方面的潜力。机理研究表明，肟酯既可以作为自由基前体，也可以作为氢原子转移试剂。
