Synthesis 2024; 56(21): 3341-3347
DOI: 10.1055/a-2302-5887
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

Photoredox-Enabled Synthesis of α-Alkylated Alkenylammonium Salts

Rina Tonedachi
a   Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Gakuen Uegahara 1, Sanda, Hyogo 669-1330, Japan
,
Aoi Yoshita
a   Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Gakuen Uegahara 1, Sanda, Hyogo 669-1330, Japan
,
Yota Sakakibara∗
a   Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Gakuen Uegahara 1, Sanda, Hyogo 669-1330, Japan
,
Kei Murakami  ∗
a   Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Gakuen Uegahara 1, Sanda, Hyogo 669-1330, Japan
b   JST PRESTO, 7 Gobancho, Chiyoda, Tokyo 102-0076, Japan
› InstitutsangabenThis work was supported by Japan Science and Technology Agency (JST) Precursory Research for Embryonic Science and Technology (PRESTO) Grant Number JPMJPR20D8 (K.M.). This work was also supported by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers 22K20545 and 23K13753 (Y.S.), the Ube Industries Foundation (K.M.), Takeda Science Foundation (K.M.), Astellas Foundation for Research on Metabolic Disorders (K.M.), and the Uehara Memorial Foundation (K.M.).
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Abstract

The development of novel synthetic methods for quaternary ammonium salts is highly demanded since the current synthesis heavily relies on the conventional Menshutkin reaction. Herein, we report photoredox-catalyzed alkylation of α-brominated alkenylammonium salts. Mechanistically, the generation of a highly reactive α-ammoniovinyl radical is the key to our method. This reaction enables the synthesis of various unprecedented α-alkylated alkenylammonium salts.

Key words

alkenylammonium salts - photoredox catalyst - alkylation - halogen-atom transfer - quaternary ammonium salts

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2302-5887.
  • Supporting Information


Publikationsverlauf

Eingereicht: 27. März 2024

Angenommen nach Revision: 09. April 2024

Accepted Manuscript online:
09. April 2024

Artikel online veröffentlicht:
23. April 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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