Radical α‑C–H\nAlkylation and Heteroarylation\nof Benzyl Anilines Enabled by Organic Photoredox Catalysis

A photocatalysis-involved α-amino radical provides\nan appealing\napproach for rapid construction of complex amine architectures. Reported\nherein is an organophotoredox catalytic approach to α-C–H\nalkylation and heteroarylation of benzyl anilines, which enables the\nintroduction of valuable trifluoromethyl alcohol, chromanone, or pyridine\nmotifs at the α position of amines. This protocol highlights\nmetal-free, step and atom economies and broad substrate scopes (>80\nexamples). Control experiments and electron paramagnetic resonance\nspectroscopy identified the α-amino radical derived from the\nα-amino C–H bond.

Publication Details

Journal
Figshare
Published
2024-12-17
DOI
https://doi.org/10.1021/acs.orglett.4c04278.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Radical α‑C–H\nAlkylation and Heteroarylation\nof Benzyl Anilines Enabled by Organic Photoredox Catalysis

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Radical Photochemical Reactions
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Radical α‑C–H\nAlkylation and Heteroarylation\nof Benzyl Anilines Enabled by Organic Photoredox Catalysis

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Abstract

A photocatalysis-involved α-amino radical provides\nan appealing\napproach for rapid construction of complex amine architectures. Reported\nherein is an organophotoredox catalytic approach to α-C–H\nalkylation and heteroarylation of benzyl anilines, which enables the\nintroduction of valuable trifluoromethyl alcohol, chromanone, or pyridine\nmotifs at the α position of amines. This protocol highlights\nmetal-free, step and atom economies and broad substrate scopes (>80\nexamples). Control experiments and electron paramagnetic resonance\nspectroscopy identified the α-amino radical derived from the\nα-amino C–H bond.

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Radical α‑C–H\nAlkylation and Heteroarylation\nof Benzyl Anilines Enabled by Organic Photoredox Catalysis · Figshare (2024) | TGRS Research Map | TGRS