Decatungstate-Photocatalyzed\nHydroamidomethylation\nof Azobenzenes with <i>N</i>,<i>N</i>‑Dimethylamides

A photocatalytic hydroamidomethylation of azobenzenes\nwith <i>N</i>,<i>N</i>-dimethylamides has been\ndeveloped.\nUsing tetrabutylammonium decatungstate (TBADT) as a photocatalyst,\nan array of azobenzenes and <i>N</i>,<i>N</i>-dimethylamides\nreacted smoothly under visible light irradiation, affording previously\nunreported <i>N</i>-amidomethyl-<i>N</i>,<i>N</i>′-diarylhydrazines in generally high yields. Mechanistic\nstudies indicate that the reaction is enabled by TBADT-mediated hydrogen\natom transfer (HAT) photocatalysis. This work is fundamentally different\nfrom the previously reported reaction of <i>N</i>,<i>N</i>-dimethylformamide with azobenzenes.

Publication Details

Journal
Figshare
Published
2024-11-19
DOI
https://doi.org/10.1021/acs.orglett.4c03931.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Decatungstate-Photocatalyzed\nHydroamidomethylation\nof Azobenzenes with N,N‑Dimethylamides

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Radical Photochemical Reactions
article

Decatungstate-Photocatalyzed\nHydroamidomethylation\nof Azobenzenes with N,N‑Dimethylamides

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Abstract

A photocatalytic hydroamidomethylation of azobenzenes\nwith <i>N</i>,<i>N</i>-dimethylamides has been\ndeveloped.\nUsing tetrabutylammonium decatungstate (TBADT) as a photocatalyst,\nan array of azobenzenes and <i>N</i>,<i>N</i>-dimethylamides\nreacted smoothly under visible light irradiation, affording previously\nunreported <i>N</i>-amidomethyl-<i>N</i>,<i>N</i>′-diarylhydrazines in generally high yields. Mechanistic\nstudies indicate that the reaction is enabled by TBADT-mediated hydrogen\natom transfer (HAT) photocatalysis. This work is fundamentally different\nfrom the previously reported reaction of <i>N</i>,<i>N</i>-dimethylformamide with azobenzenes.

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Radical Photochemical Reactions
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