Year-Long and Air Stable Radical Anion/Dianion Systems for Stereoselective (E)-Enenitrile Synthesis

11 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We present a radical anion/dianion system, octabromo N-pentyl perylenediimide (PDI-Br8), that is both year-stable and air-stable, serving as an effective visible-light photocatalyst for the stereoselective synthesis of (E)-enenitriles. This reaction proceeds through a one-pot, three-component coupling of terminal alkynes, carbon tetrahalides, and acrylonitrile under ambient conditions. The radical anion of PDI-Br8, formed using tetrabutylammonium cyanide (TBAC) in acetonitrile under blue LED irradiation. Notably, the process achieves 100% atom economy with low E-factor, underscoring its high efficiency and sustainability.

Keywords

Visible Light Photocatalysis
Year Stable Radical Anion
Three Component Coupling
Stereoselective Synthesis

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