We have developed the first example of a photoredox catalytic method for the formation of carbon-fluorine (C-F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the (3)MLCT (triplet metal-to-ligand charge transfer) state of Ru(bpy)3(2+) to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ja412083f | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Catalytic Asymmetric 1,4-Hydrocarbonation of 1,3-Enynes via Photoredox/Cobalt/Chromium Triple Catalysis.
Angew Chem Int Ed Engl
January 2025
Shanghai Jiao Tong University, Chemistry, 800 Dongchuan RD. Minhang District, 200240, Shanghai, CHINA.
A synergistic photoredox/cobalt/chromium triple catalysis system for regioselective, enantioselective, and diastereoselective 1,4-hydrocarbonation of readily available 1,3-enyne precursors was explored, providing a modular synthetic platform for various trisubstituted axially chiral allenes bearing an extra central chirality. The protocol features a broad substrate scope, good functional group tolerance, excellent selectivity, and mild reaction conditions. Furthermore, a possible reaction mechanism is proposed based on numerous control experiments and density functional theory calculations.
View Article and Find Full Text PDFEnzymatic Cascades for Stereoselective and Regioselective Amide Bond Assembly.
Angew Chem Int Ed Engl
January 2025
The University of Manchester, School of Chemistry & Manchester Institute of Biotechnology, 131 Princess Street, M1 7DN, Manchester, UNITED KINGDOM OF GREAT BRITAIN AND NORTHERN IRELAND.
Amide bond formation is fundamental in nature and is widely used in the synthesis of pharmaceuticals and other valuable products. Current methods for amide synthesis are often step and atom inefficient, requiring the use of protecting groups, deleterious reagents and organic solvents that create significant waste. The development of cleaner and more efficient catalytic methods for amide synthesis remains an urgent unmet need.
View Article and Find Full Text PDFAminoalkylation of Alkenes Enabled by Triple Radical Sorting.
J Am Chem Soc
January 2025
Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.
The direct synthesis of C(sp)-rich architectures is a driving force for innovation in synthetic organic chemistry. Such scaffolds impart beneficial properties onto drug molecules that correlate with greater clinical success. Consequently, there is a strong impetus to develop new methods by which to access sp-rich molecules from commercial feedstocks, such as alkenes.
View Article and Find Full Text PDFIntracellular Co-Delivery of Carbon Monoxide and Nitric Oxide Induces Mitochondrial Apoptosis for Cancer Therapy.
Angew Chem Int Ed Engl
January 2025
University of Science and Technology of China, Department of Polymer Science and Engineering, 96 Jinzhai Road, 230026, , 230026, Hefei, CHINA.
Understanding the interplay between gasotransmitters is essential for unlocking their therapeutic potential. However, achieving spatiotemporally controlled co-delivery to target cells remains a significant challenge. Herein, we propose an innovative strategy for the intracellular co-delivery of carbon monoxide (CO) and nitric oxide (NO) gasotransmitters under clinically relevant wavelengths.
View Article and Find Full Text PDFMetallaphotoredox Enabled Single Carbon Atom Insertion into Alkenes for Allene Synthesis.
Angew Chem Int Ed Engl
January 2025
Westlake University, Chemistry, No.18 Shilongshan Road, 310024, Hangzhou, CHINA.
Efficient methods for synthesizing allenes from readily available starting materials pose a persistent challenge in organic chemistry. In this work, we present a novel two-stage protocol for allene synthesis involving the single-atom insertion into alkenes, facilitated by synergistic photoredox and cobalt catalysis. Diverging from conventional methods such as the Doering-LaFlamme reaction, this photochemical rearrangement approach operates efficiently under mild conditions in a radical-based manner.
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!