A new era for homolytic aromatic substitution: replacing Bu3SnH with efficient light-induced chain reactions

2016 ◽  
Vol 14 (16) ◽  
pp. 3849-3862 ◽  
Author(s):  
Michael Gurry ◽  
Fawaz Aldabbagh
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Aromatic Substitution ◽  
New Era ◽  
Chain Reactions ◽  
Radical Initiator ◽  
Aromatic Heterocycles ◽  
Recent Advances ◽  
Homolytic Aromatic Substitution

Recent advances such as visible-light photoredox catalysis have largely superseded radical initiator-mediated substitutions onto arenes and aromatic heterocycles.

Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms

Synthesis ◽  
2019 ◽  
Vol 51 (14) ◽  
pp. 2759-2791 ◽  
Author(s):  
Jian-Quan Liu ◽  
Andrey Shatskiy ◽  
Bryan S. Matsuura ◽  
Markus D. Kärkäs
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Hypervalent Iodine ◽  
Amino Acid Residues ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Specific Amino Acid ◽  
Recent Advances ◽  
Redox Active ◽  
Decarboxylative Coupling

The selective modification of α-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues.1 Introduction2 Visible-Light-Mediated Functionalization of α-Amino Acids2.1 Decarboxylative Functionalization Involving Redox-Active Esters2.2 Direct Decarboxylative Coupling Strategies2.3 Hypervalent Iodine Reagents2.4 Dual Photoredox and Transition-Metal Catalysis2.5 Amination and Deamination Strategies3 Photoinduced Peptide Diversification3.1 Gese-Type Bioconjugation Methods3.2 Peptide Macrocyclization through Photoredox Catalysis3.3 Biomolecule Conjugation through Arylation3.4 C–H Functionalization Manifolds4 Conclusions and Outlook

scholarly journals Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 7051
Author(s):  
Lei Zhou
Keyword(s):  
Visible Light ◽  
Future Development ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Benign ◽  
Personal Perspective ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
The Future ◽  
The Creation

The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided.

scholarly journals Recent Advances of Dicyanopyrazine (DPZ) in Photoredox Catalysis

Photochem ◽  
2021 ◽  
Vol 1 (2) ◽  
pp. 237-246
Author(s):  
Vishal Srivastava ◽  
Pravin K. Singh ◽  
Arjita Srivastava ◽  
Surabhi Sinha ◽  
Praveen P. Singh
Keyword(s):  
Catalytic Activity ◽  
Visible Light ◽  
Organic Synthesis ◽  
Chemical Environment ◽  
Organic Substrates ◽  
Photoredox Catalysis ◽  
Organic Transformations ◽  
Recent Advances ◽  
Invaluable Tool ◽  
Unique Chemical

Visible light organophotoredox catalysis has emerged as an invaluable tool for organic synthetic transformations since it works brilliantly in tandem with organic substrates and has been known to create unique chemical environment for organic transformations. Dicyanopyrazine (DPZ), a relatively lesser researched organophotoredox catalyst, has shown great potential through its catalytic activity in organic synthesis and necessitates attention of synthetic community.

Remote C–C bond formation via visible light photoredox-catalyzed intramolecular hydrogen atom transfer

2020 ◽  
Vol 18 (24) ◽  
pp. 4519-4532 ◽  
Author(s):  
Hui Chen ◽  
Shouyun Yu
Keyword(s):  
Hydrogen Atom ◽  
Visible Light ◽  
Bond Formation ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
Intramolecular Hydrogen

Visible light photoredox catalysis combined with intramolecular hydrogen atom transfer (HAT) can serve as a unique tool for achieving remote C–C bond formation. Recent advances in photoredox-catalyzed remote C–C bond formation are summarized.

scholarly journals Recent advances in dual transition metal–visible light photoredox catalysis

2016 ◽  
Vol 57 (41) ◽  
pp. 4505-4513 ◽  
Author(s):  
Balázs L. Tóth ◽  
Orsolya Tischler ◽  
Zoltán Novák
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Photoredox Catalysis ◽  
Recent Advances

scholarly journals Amine α-heteroarylation via photoredox catalysis: a homolytic aromatic substitution pathway

2014 ◽  
Vol 5 (11) ◽  
pp. 4173-4178 ◽  
Author(s):  
Christopher K. Prier ◽  
David W. C. MacMillan
Keyword(s):  
Tertiary Amines ◽  
Photoredox Catalysis ◽  
Aromatic Substitution ◽  
Homolytic Aromatic Substitution

The direct α-heteroarylation of tertiary amines has been accomplished via photoredox catalysis to generate valuable benzylic amine pharmacophores.

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