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Synthesis 2024; 56(21): 3341-3347
DOI: 10.1055/a-2302-5887
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
This 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.).
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 saltsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2302-5887.
- Supporting Information
Publication History
Received: 27 March 2024
Accepted after revision: 09 April 2024
Accepted Manuscript online:
09 April 2024
Article published online:
23 April 2024
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