Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Visible-Light-Mediated Synthesis of Oxidized Amides via Organic Photoredox Catalysis

Synthesis ◽

10.1055/s-0036-1591988 ◽

2018 ◽

Vol 50 (17) ◽

pp. 3379-3386 ◽

Cited By ~ 1

Author(s):

Ting Wang ◽

Yuliu Du ◽

Zheng Wei

Keyword(s):

Amino Acids ◽

Visible Light ◽

Functional Groups ◽

Photoredox Catalysis ◽

Reaction Conditions

The development of visible-light-mediated synthesis of oxidized amides is reported. The reaction shows a broad substrate scope and highlights a mild nature of the reaction conditions. A range of functional groups are well tolerated in the reaction. Relying on the strategy, a variety of α-alkoxy amino acids are synthesized.

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α-Functionalization of Imines via Visible Light Photoredox Catalysis

Catalysts ◽

10.3390/catal10050562 ◽

2020 ◽

Vol 10 (5) ◽

pp. 562 ◽

Cited By ~ 4

Author(s):

Alberto F. Garrido-Castro ◽

M. Carmen Maestro ◽

José Alemán

Keyword(s):

Visible Light ◽

Building Blocks ◽

Single Electron ◽

Synthetic Chemistry ◽

Photoredox Catalysis ◽

Reaction Conditions ◽

Radical Intermediates ◽

Research Programs ◽

Electron Reduction

The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.

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A Multiphoton Single-Electron Reduction of Olefins via Tandem Photoredox Catalysis

10.26434/chemrxiv.12235928.v1 ◽

2020 ◽

Author(s):

Tyra Horngren ◽

Mitchell S. Taylor ◽

Milena Czyz ◽

Anastasios Polyzos

Keyword(s):

Visible Light ◽

Radical Anion ◽

Hydrogen Gas ◽

Single Electron ◽

Photoredox Catalysis ◽

Reaction Conditions ◽

Electron Reduction

<a></a>Herein we report a visible light multiphoton tandem photoredox catalysis strategy enabling a distinctive mode of olefin activation via a one electron reduction to the corresponding radical anion. This highly nucleophilic intermediate was harnessed to develop a method for the formal hydrogenation of unactivated alkenes under mild reaction conditions, in the absence of hydrogen gas or dissolving metals.

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A Multiphoton Single-Electron Reduction of Olefins via Tandem Photoredox Catalysis

10.26434/chemrxiv.12235928 ◽

2020 ◽

Author(s):

Tyra Horngren ◽

Mitchell S. Taylor ◽

Milena Czyz ◽

Anastasios Polyzos

Keyword(s):

Visible Light ◽

Radical Anion ◽

Hydrogen Gas ◽

Single Electron ◽

Photoredox Catalysis ◽

Reaction Conditions ◽

Electron Reduction

<a></a>Herein we report a visible light multiphoton tandem photoredox catalysis strategy enabling a distinctive mode of olefin activation via a one electron reduction to the corresponding radical anion. This highly nucleophilic intermediate was harnessed to develop a method for the formal hydrogenation of unactivated alkenes under mild reaction conditions, in the absence of hydrogen gas or dissolving metals.

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Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

10.26434/chemrxiv.7796603.v1 ◽

2019 ◽

Cited By ~ 1

Author(s):

Arumugavel Murugan ◽

Venkata Nagarjuna Babu ◽

Nagaraj Sabarinathan ◽

Sharada Duddu. S

Keyword(s):

Transition Metal ◽

Visible Light ◽

Practical Approach ◽

Hypervalent Iodine ◽

Radical Mechanism ◽

Photoredox Catalysis ◽

Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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Faculty Opinions recommendation of Batch to flow deoxygenation using visible light photoredox catalysis.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.718012691.793477212 ◽

2013 ◽

Author(s):

Steven L Castle

Keyword(s):

Visible Light ◽

Photoredox Catalysis

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Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽

10.1055/a-1343-6541 ◽

2020 ◽

Author(s):

Jia-Jia Zhao ◽

Hong-Hao Zhang ◽

Shouyun Yu

Keyword(s):

Visible Light ◽

Asymmetric Synthesis ◽

Carbonyl Compounds ◽

Asymmetric Reduction ◽

Chemical Transformations ◽

Photoredox Catalysis ◽

Radical Coupling ◽

Mild Conditions ◽

Iminium Ions ◽

Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

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