Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts

Arockiam, Percia Beatrice and Lennert, Ulrich and Graf, Christina and Rothfelder, Robin and Scott, Daniel J. and Fischer, Tillmann G. and Zeitler, Kirsten and Wolf, Robert (2020) Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts. CHEMISTRY-A EUROPEAN JOURNAL, 26 (69). pp. 16374-16382. ISSN 0947-6539, 1521-3765

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Abstract

Asymmetrically substituted tertiary phosphines and quaternary phosphonium salts are used extensively in applications throughout industry and academia. Despite their significance, classical methods to synthesize such compounds often demand either harsh reaction conditions, prefunctionalization of starting materials, highly sensitive organometallic reagents, or expensive transition-metal catalysts. Mild, practical methods thus remain elusive, despite being of great current interest. Herein, we describe a visible-light-driven method to form these products from secondary and primary phosphines. Using an inexpensive organic photocatalyst and blue-light irradiation, arylphosphines can be both alkylated and arylated using commercially available organohalides. In addition, the same organocatalyst can be used to transform white phosphorus (P-4) directly into symmetrical aryl phosphines and phosphonium salts in a single reaction step, which has previously only been possible using precious metal catalysis.

Item Type: Article
Uncontrolled Keywords: CATALYZED SYNTHESIS; INTERMOLECULAR HYDROPHOSPHINATION; IONIC LIQUIDS; EASY ACCESS; ARYL; COMPLEXES; CONVENIENT; ALKENES; LIGAND; ALKYL; alkylation; arylation; phosphane; phosphorus; photocatalysis
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie > Arbeitskreis Prof. Dr. Robert Wolf
Depositing User: Dr. Gernot Deinzer
Date Deposited: 08 Mar 2021 11:15
Last Modified: 08 Mar 2021 11:15
URI: https://pred.uni-regensburg.de/id/eprint/43501

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