Reactivity of triplet diradical intermediates in aqueous media for transition-metal-free Csp2–H alkylationopen access
- Authors
- Ghosh, Prithwish; Byun, Youjung; Kwon, Na Yeon; Kang, Ju Young; Mishra, Neeraj Kumar; Park, Jung Su; Kim, In Su
- Issue Date
- Apr-2022
- Publisher
- Cell Press
- Keywords
- alkylation; diradicals; N-heterocycles; nitrogen ylides; pyridinium salts
- Citation
- Cell Reports Physical Science, v.3, no.4
- Journal Title
- Cell Reports Physical Science
- Volume
- 3
- Number
- 4
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/152791
- DOI
- 10.1016/j.xcrp.2022.100819
- ISSN
- 2666-3864
2666-3864
- Abstract
- Alkyl pyridinium salts have been used in dipolar cycloaddition reactions with π-unsaturated compounds and in reductive single-electron transfer reactions as convenient radical precursors. Here, we report a distinct reaction pathway involving triplet diradical intermediates in the coupling reaction between alkyl pyridinium ylides and electrophilic N-heterocyclic molecules. We demonstrate that alkyl pyridinium ylides generated from alkyl pyridinium salts under basic aqueous conditions can undergo addition into iminoamido N-heterocycles, generating triplet diradical intermediates that can lead to C–H alkylated products. The proposed reaction mechanism is supported by electron paramagnetic resonance and radical scavenging experiments. Notably, a wide substrate scope and excellent level of functional group tolerance are attained under cost-effective and straightforward conditions, which reveal the amenability of this protocol in the pharmaceutical and chemical industries. © 2022 The Authors
- Files in This Item
-
Go to Link
- Appears in
Collections - 이과대학 > 화학과 > 1. Journal Articles
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.