Issue 18, 2023

Photoinduced synthesis of C2-linked phosphine oxides via radical difunctionalization of acetylene

Abstract

Herein, we report a photocatalyzed radical difunctionalization of acetylene for the rapid synthesis of C2-linked phosphine compounds. The reaction was initiated by addition of a phosphinoyl radical, followed by two cascade transformations. One involves a double addition for the formation of DPPE-dioxide analogues and in the other the intermediate vinylphosphine oxide is intercepted by a radical formed from an oxoheterocycle. This method features metal-free and mild conditions (rt, 1 atm acetylene), 100% atom economy and easy operation. Furthermore, the reaction can be robustly performed on a decagram scale.

Graphical abstract: Photoinduced synthesis of C2-linked phosphine oxides via radical difunctionalization of acetylene

Supplementary files

Article information

Article type
Paper
Submitted
28 Jul 2023
Accepted
07 Aug 2023
First published
07 Aug 2023

Green Chem., 2023,25, 7253-7258

Photoinduced synthesis of C2-linked phosphine oxides via radical difunctionalization of acetylene

K. Li, J. Deng, X. Long and S. Zhu, Green Chem., 2023, 25, 7253 DOI: 10.1039/D3GC02794E

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