Herein, we investigate the use of organic photocatalysts in the visible light-promoted β-functionalization of carbonyl compounds. In particular, we studied the addition of aliphatic aldehydes to α,β-unsaturated compounds (β-Michael addition), and the reaction of cyclic ketones with either ketones (β-aldol condensation) or imines (β-Mannich reaction). Among the dyes tested, donor-acceptor cyanoarenes gave the best results, promoting the transformations of interest in moderate to good yields. The reaction scope was investigated on substrates with different steric and electronic properties. Fluorescence quenching analysis (Stern-Volmer experiments) led us to propose for these reactions a reductive quenching mechanism involving a transient 5πe activation mode.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594657 | PMC |
| http://dx.doi.org/10.1021/acs.joc.3c00890 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Visible-light-promoted azidation/arylation of unactivated alkenes with Togni-N electron donor-acceptor complexes.
Org Biomol Chem
January 2025
Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China.
A visible-light-promoted azidation/arylation of unactivated alkenes with Togni-N has been achieved, leading to a series of azidated pyrrolo[1,2-]indoles under photocatalyst-free conditions. Notably, an EDA complex derived from the electron-rich indole derivatives and Togni-N served as the key intermediate in this reaction.
View Article and Find Full Text PDFEnhanced oxidative potential and SO heterogeneous oxidation on candle soot after photochemical aging: Influencing mechanisms of different irradiation wavelengths.
Environ Pollut
December 2024
School of Environmental Science and Engineering, Changzhou University, Changzhou, 213164, China; Key Laboratory of Advanced Plasma Catalysis Engineering for China Petrochemical Industry, Jiangsu, 213164, China. Electronic address:
Photochemistry plays a significant role in the atmospheric aging processes of soot. However, the physicochemical properties and changes in environmental and health effects of soot particles from sacrificial sources after photochemical aging remain unclear. The reaction mechanisms of soot under different irradiation wavelengths require further investigation.
View Article and Find Full Text PDFContinuous activation of phenoxide and CFI for multiple trifluoromethylations.
Chem Commun (Camb)
January 2025
Graduate School of Science and Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi, 755-8611, Japan.
The introduction of multiple trifluoromethyl (CF) groups into aromatic compounds remains a significant challenge in synthetic chemistry. Here, we report an unprecedented visible light-promoted multiple trifluoromethylation of phenols using commercially available CFI. The key to success lies in our discovery of a "continuous activation strategy" that enables sequential trifluoromethylations through single-electron transfer from photoexcited phenoxide to CFI until all or positions are occupied.
View Article and Find Full Text PDFVisible-Light-Induced Markovnikov Hydroalkoxylation of α-Trifluoromethyl Alkenes with -Diketones.
J Org Chem
December 2024
Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, P. R. China.
We report, for the first time, a visible-light-promoted Markovnikov hydroalkoxylation of α-trifluoromethyl alkenes with 1,2-diketones. This transformation proceeded smoothly in the presence of a tertiary amine (EtN), providing a series of enol ethers containing the trifluoromethylated tetrasubstituted center in moderate to excellent yields. In this protocol, hydrogen atom transfer between this amine and 1,2-diketone substrate affords a ketyl radical and an α-aminoalkyl radical, which engages in the formation of a radical anion of the α-CF alkene via a single electron transfer.
View Article and Find Full Text PDFCopper-Catalyzed Asymmetric C(sp)-H Benzylation: Stereoselective Synthesis of Unnatural Aromatic Amino Acids.
Org Lett
December 2024
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, 199 West Donggang Road, Lanzhou 730000, China.
The general synthesis of chiral unnatural aromatic amino acids has rarely been reported. We herein describe a visible light-promoted copper-catalyzed enantioselective C(sp)-H benzylation of glycine derivatives. The method demonstrated compatibility in coupling various -hydroxyphthalimide (NHP) esters derived from aromatic acids with glycine derivatives, providing a general protocol for synthesizing analogues of phenylalanine, tryptophan, and tyrosine.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!