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

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-dio...

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Bibliographic Details
Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 25; no. 18; pp. 7253 - 7258
Main Authors Li, Kangkui, Deng, Jiazhen, Long, Xianyang, Zhu, Shifa
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.09.2023
Royal Society of Chemistry
Subjects
Acetylene
Atom economy
Chemistry
Chemistry, Multidisciplinary
Green & Sustainable Science & Technology
Green chemistry
Phosphine
Phosphine oxide
Physical Sciences
Science & Technology
Science & Technology - Other Topics
Synthesis
ACTIVATION
LIGANDS
ACIDS
ALKYLATION
COMPLEXES
CHEMISTRY
CONVENIENT
ALDEHYDES
ALKYNES
PHOTOREDOX CATALYSIS
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc02794e