Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
We herein describe a simple approach for generating acyl radical from acyl chloride via photoinduced single-electron transfer. It has been demonstrated that the generated acyl radicals could react with various substrates, including isocyanides, methacrylamides, alkenes, alkynes, and enynes, to afford diverse heterocycles (>10 classes). Mechanistic analyses show that a photoactive charge transfer complex between acyl chloride and a Lewis base additive is involved in enabling the photogeneration of the acyl radical. The study exemplifies a new and simple method of photoactivation of carbonyl compounds.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.2c03339 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photochemical Synthesis of Ynones from Aryl Aldehydes and Sulfone-Based Alkynes.
J Org Chem
September 2025
School of Chemistry, O'Brien Centre for Science, University College Dublin, Dublin 4, Belfield D04 N2E5, Ireland.
Ynones are attractive molecular building blocks owing to their electrophilic character, which can be exploited in a variety of functionalization strategies, giving rise to valuable reaction products. This work presents a photochemical strategy for the direct generation of ynones from aldehydes and substituted alkynes bearing radicofugal groups, such as sulfones. Using TBADT (tetrabutylammonium decatungstate) as a photocatalyst, the direct photochemical synthesis of a variety of ynones is achieved in high yields and short reaction times.
View Article and Find Full Text PDFOrganocatalysis promoted by 1,2,3-triazolylidenes (MICs): carbenes which make a difference.
Chem Soc Rev
September 2025
Department of Chemistry and Biochemistry, UCSD-CNRS Joint Research Laboratory (IRL3555), University of California, San Diego, La Jolla, CA 92093-0358, USA.
N-Heterocyclic carbenes (NHCs) hold a unique significance in organometallic catalysis and are powerful organocatalysts for a variety of organic transformations involving crucial intermediates such as Breslow intermediates (BIs), deprotonated BIs (BI-s), ketyl radicals (KRs), and acyl azoliums (AAs). To address the remaining challenges facing reactions catalyzed by NHCs, non-classical stable carbenes, namely 1,2,3-triazolylidenes (MICs), cousins of NHCs, have shown great potential. MICs share similar features with typical NHCs but possess unique characteristics, such as enhanced σ-donor ability and absence of dimerization.
View Article and Find Full Text PDFVisible-Light-Promoted Hydroxyalkylation of Heterocycles with α-Oxocarboxylic Acids.
J Org Chem
September 2025
College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China.
We herein report the Minisci-type redox-neutral decarboxylative hydroxyalkylation of heteroarenes under photocatalyst- and transition-metal-free conditions. This methodology tolerates various functional groups that can be subsequently elaborated. Upon absorption of photons, the excited state of the α-oxocarboxylic acid forms an acyl radical, which adds to the protonated heteroarene to give the desired product after a spin center shift (SCS), reduction, and deprotonation.
View Article and Find Full Text PDFVisible-Light-Mediated Radical Cascade Iodotrifluoroethylation and Acylation/Cyclization of -Tethered 1,6-Enynes with 1,1,1-Trifluoro-2-iodoethane and Acyl Oxime Esters.
J Org Chem
September 2025
Yunnan Key Laboratory of Modern Separation Analysis and Substance Transformation, College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming, Yunnan Province 650500, P. R. China.
Photoinduced trifluoroethyl and acyl radical procedures for the efficient and simple preparation of iodotrifluoroethylated and acylated pyrrolidine-2-ones from -tethered 1,6-enynes with 1,1,1-trifluoro-2-iodoethane and acyl oxime esters are reported. The photoinduced iodotrifluoroethylation is performed via the energy transfer (EnT) process of the fluorescein sodium-mediated atom-transfer radical addition (ATRA) strategy under visible-light irradiation. The acylation is carried out with 4CzIPN as an organophotocatalyst at room temperature under metal- and oxidant-free conditions.
View Article and Find Full Text PDFThree-Component Synthesis of γ-Amino Esters with α-Quaternary Carbon Centers via NHC/Photoredox Dual Catalysis.
Adv Synth Catal
July 2025
Department of Chemistry, Northwestern University, Evanston, United States.
γ-Amino acid derivatives are important motifs in medicinal chemistry and have shown wide applicability as inhibitory neurotransmitters. An important class of these compounds feature α,α-disubstitution. However, established routes for the direct synthesis of γ-amino esters bearing α-quaternary centers are severely limited in both number of available routes and scope of the transformation.
View Article and Find Full Text PDF