We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Photocatalytic C(sp<sup>3</sup>)‐H gem‐Difluoroallylation and Alkylation with Alkenes via a Base‐Assisted Formal 1,2‐Hydrogen Atom Transfer of Amidyl Radicals.
- Authors
Tang, Meifang; Feng, Bingbing; Bao, Yanyang; Xu, Zhongtian; Huang, Chao; Zheng, Hanliang; Zhu, Gangguo; Wang, Yanan; Yuan, Zheliang
- Abstract
Comprehensive Summary: Compared to well‐established 1,5‐HAT of N‐centered radicals, the synthetic applications of 1,2‐HAT process were scarce due to the high barrier and constrained three‐membered transition state. Here, we have developed a novel C(sp3)‐H gem‐difluoroallylation via a base assisted formal 1,2‐HAT of amidyl radicals with the reductive quenching cycle of photocatalyst. This transformation enables the efficient formation of α‐aminoalkyl radicals via 1,2‐HAT and showcases good functional group tolerance. Our preliminary mechanistic experiments, along with Density Functional Theory (DFT) calculations demonstrate the feasibility of 1,2‐HAT of amidyl radicals, especially when assisted by a base. Furthermore, our method also succeeds in the Giese addition of electron‐deficient alkenes as well as styrene.
- Subjects
RADICALS (Chemistry); DENSITY functional theory; FUNCTIONAL groups; ALKENES; PHOTOCATALYSIS
- Publication
Chinese Journal of Chemistry, 2024, Vol 42, Issue 18, p2203
- ISSN
1001-604X
- Publication type
Article
- DOI
10.1002/cjoc.202400122