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

Author:

Soutome HirokiORCID,Yamashita Hiroki,Shimizu Yutaka,Takumi Masahiro,Ashikari YosukeORCID,Nagaki AiichiroORCID

Abstract

AbstractIn 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.

Funder

MEXT | Japan Society for the Promotion of Science

Japan Agency for Medical Research and Development

New Energy and Industrial Technology Development Organization

MEXT | JST | Core Research for Evolutional Science and Technology

Ogasawara Foundation for the Promotion of Science and Engineering

Publisher

Springer Science and Business Media LLC

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