Convergent approach for direct cross-coupling enabled by flash irreversible generation of cationic and anionic species

Hiroki Soutome, Hiroki Yamashita, Yutaka Shimizu, Masahiro Takumi, Yosuke Ashikari and Aiichiro Nagaki ()
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Hiroki Soutome: Hokkaido University
Hiroki Yamashita: Hokkaido University
Yutaka Shimizu: Hokkaido University
Masahiro Takumi: Hokkaido University
Yosuke Ashikari: Hokkaido University
Aiichiro Nagaki: Hokkaido University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract In biosynthesis multiple kinds of reactive intermediates are generated, transported, and reacted across different parts of organisms, enabling highly sophisticated synthetic reactions. Herein we report a convergent synthetic approach, which utilizes dual intermediates of cationic and carbanionic species in a single step, hinted at by the ideal reaction conditions. By reactions of unsaturated precursors, such as enamines, with a superacid in a flow microreactor, cationic species, such as iminium ions, are generated rapidly and irreversibly, and before decomposition, they are transported to react with rapidly and independently generated carbanions, enabling direct C-C bond formation. Taking advantage of the reactivity of these double reactive intermediates, the reaction take place within a few seconds, enabling synthetic reactions which are not applicable in conventional reactions.

Date: 2024
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DOI: 10.1038/s41467-024-48723-1

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