scholarly journals Visible light photoredox-catalyzed deoxygenation of alcohols

2014 ◽  
Vol 10 ◽  
pp. 2157-2165 ◽  
Author(s):  
Daniel Rackl ◽  
Viktor Kais ◽  
Peter Kreitmeier ◽  
Oliver Reiser
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Blue Light ◽  
Functional Group ◽  
Bond Cleavage ◽  
Environmentally Benign ◽  
Visible Light Photocatalysis ◽  
Water Mixture ◽  
Visible Light Photocatalyst ◽  
Single Bonds

Carbon–oxygen single bonds are ubiquitous in natural products whereas efficient methods for their reductive defunctionalization are rare. In this work an environmentally benign protocol for the activation of carbon–oxygen single bonds of alcohols towards a reductive bond cleavage under visible light photocatalysis was developed. Alcohols were activated as 3,5-bis(trifluoromethyl)-substituted benzoates and irradiation with blue light in the presence of [Ir(ppy)2(dtb-bpy)](PF6) as visible light photocatalyst and Hünig’s base as sacrificial electron donor in an acetonitrile/water mixture generally gave good to excellent yields of the desired defunctionalized compounds. Functional group tolerance is high but the protocol developed is limited to benzylic, α-carbonyl, and α-cyanoalcohols; with other alcohols a slow partial C–F bond reduction in the 3,5-bis(trifluoromethyl)benzoate moiety occurs.

Visible light photocatalysis in synthesis of pharmaceutically relevant heterocyclic scaffolds

2022 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin Kumar Singh ◽  
Shraddha Tivari ◽  
Praveen Pratap Singh
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Chemical Bond ◽  
Organic Synthesis ◽  
Bond Formation ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Chemical Bond Formation

Visible light and photoredox catalysis have emerged as a powerful and long-lasting tool for organic synthesis, demonstrating the importance of a variety of chemical bond formation methods. Natural products, physiologically...

scholarly journals Direct sulfonylation of anilines mediated by visible light

2018 ◽  
Vol 9 (3) ◽  
pp. 629-633 ◽  
Author(s):  
Tarn C. Johnson ◽  
Bryony L. Elbert ◽  
Alistair J. M. Farley ◽  
Timothy W. Gorman ◽  
Christophe Genicot ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions

Visible light photocatalysis allows the introduction of the sulfone functional group to anilines under mild reaction conditions, without the need for pre-functionalization.

scholarly journals Tyrosine and Drug-like Late-stage Benzylic Functionalization via Photoredox Catalysis

2020 ◽  
Author(s):  
Tobias Brandhofer ◽  
Volker Derdau ◽  
María Mendez ◽  
Christoph Pöverlein ◽  
Olga Garcia Mancheno
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Functional Group ◽  
Reaction Conditions ◽  
Site Selectivity ◽  
Wide Range ◽  
High Yields ◽  
Therapeutic Compounds

Abstract Visible light mediated late-stage functionalization is a rising field in synthetic and medicinal chemistry, allowing the fast and diversified modification of valuable, potentially therapeutic compounds such as peptides. However, there are relatively few mild methodologies for the C(sp3)-H functionalization of complex peptides. Herein, we report a visible light mediated photocatalytic protocol for the benzylic C-H modification of tyrosine and related C-H bonds. The embraced radical-cation/deprotonation strategy enables an incorporation of a wide range of valuable functional groups in high yields and chemoselectivity. The mild reaction conditions, site-selectivity and high functional group tolerance was highlighted by the functionalization of complex peptides, drugs and natural products, providing a promising synthetic platform in medicinal chemistry.

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.

Visible-Light-Mediated Multicomponent Reaction for Secondary Amine Synthesis

2021 ◽  
Author(s):  
Qingmin Wang ◽  
Xiaochen Wang ◽  
Binbing Zhu ◽  
Jianyang Dong ◽  
hao tian ◽  
...  
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Small Molecule ◽  
Secondary Amine ◽  
Multicomponent Reaction ◽  
Functional Group ◽  
Secondary Amines ◽  
Biological Probes

The widespread presence of secondary amines in agrochemicals, pharmaceuticals, natural products, and small-molecule biological probes has inspired efforts to streamline the synthesis of molecules with this functional group. Herein, we...

Fe3O4/ZnFe2O4 micro/nanostructures and their heterogeneous efficient Fenton-like visible-light photocatalysis process

2018 ◽  
Vol 42 (5) ◽  
pp. 3736-3747 ◽  
Author(s):  
Jie Liu ◽  
Gang Liu ◽  
Chunyan Yuan ◽  
Lin Chen ◽  
Xingyou Tian ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Photocatalysis ◽  
Visible Light Photocatalyst ◽  
Highly Efficient

A Fenton-like visible-light photocatalyst composed of Fe3O4/ZnFe2O4 micro/nanostructures shows highly efficient photocatalysis in the degradation of R6G.

scholarly journals Visible light mediated photocatalytic [2 + 2] cycloaddition/ring-opening rearomatization cascade of electron-deficient azaarenes and vinylarenes

2020 ◽  
Vol 3 (1) ◽  
Author(s):  
Noelia Salaverri ◽  
Rubén Mas-Ballesté ◽  
Leyre Marzo ◽  
José Alemán
Keyword(s):  
Natural Products ◽  
Double Bond ◽  
Visible Light ◽  
Bioactive Compounds ◽  
Late Stage ◽  
Ring Opening ◽  
Functional Group ◽  
Theoretical Calculations ◽  
Double Bonds ◽  
Heterocyclic Derivatives

Abstract The broad presence of azaarene moieties in natural products has promoted the development of new functionalization reactions, giving access to larger libraries of bioactive compounds. The light promoted [2 + 2] photocycloaddition reaction to generate cyclobutanes has been extensively studied in photochemistry. In particular, De Mayo reported the [2 + 2] cycloaddition followed by retroaldol condensation between enols of 1,3-dicarbonyls and double bonds to synthesize 1,5-dicarbonyls. Herein, we describe the [2 + 2] photocycloaddition followed by a ring-opening rearomatization reaction between electron-deficient 2-methylene-azaarenes and double bonds, taking advantage of the ability of these heterocyclic derivatives to form the corresponding pseudo-enamine intermediate. The procedure shows a high functional group tolerance either on the double bond or the heteroarene side and allows the presence of different electron-withdrawing groups. In addition, the wide applicability of this reaction has been demonstrated through the late-stage derivatization of several natural products. Photochemical studies, together with theoretical calculations, support a mechanism involving the photosensitization of the pseudo-enamine intermediate.

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