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Literature DB >> 27321136

Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins.

Anthony Millet¹, Quentin Lefebvre¹, Magnus Rueping^2,3.

Abstract

A tin- and halide-free, visible-light photoredox-catalyzed Giese reaction was developed. Primary and secondary α-amino radicals were generated readily from amino acids in the presence of catalytic amounts of an iridium photocatalyst. The reactivity of the α-amino radicals has been evaluated for the functionalization of a variety of activated olefins.

Entities: Chemical

Keywords: amino acid; decarboxylation; heterocycles; photoredox catalysis

Mesh：

Substances：

Year: 2016 PMID： 27321136 DOI： 10.1002/chem.201602257

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

13 in total

1. Developments in Photoredox-Mediated Alkylation for DNA-Encoded Libraries.

Authors: Shivani Patel; Shorouk O Badir; Gary A Molander
Journal: Trends Chem Date: 2020-12-29

2. Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

Authors: L Candish; M Freitag; T Gensch; F Glorius
Journal: Chem Sci Date: 2017-02-27 Impact factor: 9.825

3. Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

Authors: Adam Noble; Riccardo S Mega; Daniel Pflästerer; Eddie L Myers; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2018-01-26 Impact factor: 15.336

Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived α-Amino Radicals to Electron-Deficient Olefins.

1. Developments in Photoredox-Mediated Alkylation for DNA-Encoded Libraries.

2. Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

3. Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

4. Silyl-mediated photoredox-catalyzed Giese reaction: addition of non-activated alkyl bromides.

5. Visible light-promoted CO₂ fixation with imines to synthesize diaryl α-amino acids.

6. Enantioselective radical conjugate additions driven by a photoactive intramolecular iminium-ion-based EDA complex.

7. Catalytic enantioselective radical coupling of activated ketones with N-aryl glycines.

8. A Redox-Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions.

9. Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling.

Review 10. Radical-Based Synthesis and Modification of Amino Acids.