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- Title
Photocatalytic Carboxylation of C−N Bonds in Cyclic Amines with CO<sub>2</sub> by Consecutive Visible‐Light‐Induced Electron Transfer.
- Authors
Chen, Lin; Qu, Quan; Ran, Chuan‐Kun; Wang, Wei; Zhang, Wei; He, Yi; Liao, Li‐Li; Ye, Jian‐Heng; Yu, Da‐Gang
- Abstract
Visible‐light photocatalytic carboxylation with CO2 is highly important. However, it still remains challenging for reluctant substrates with low reduction potentials. Herein, we report a novel photocatalytic carboxylation of C−N bonds in cyclic amines with CO2 via consecutive photo‐induced electron transfer (ConPET). It is also the first photocatalytic reductive ring‐opening reaction of azetidines, pyrrolidines and piperidines. This strategy is practical to transform a variety of easily available cyclic amines to valuable β‐, γ‐, δ‐ and ϵ‐amino acids in moderate‐to‐excellent yields. Moreover, the method also features mild and transition‐metal‐free conditions, high selectivity, good functional‐group tolerance, facile scalability and product derivations. Mechanistic studies indicate that the ConPET might be the key to generating highly reactive photocatalysts, which enable the reductive activation of cyclic amines to generate carbon radicals and carbanions as the key intermediates.
- Subjects
CARBOXYLATION; CHARGE exchange; RING-opening reactions; AMINES; REDUCTION potential; CARBANIONS
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 11, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202217918