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Versatile Visible‐Light‐Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts
Author(s) -
Arockiam Percia Beatrice,
Lennert Ulrich,
Graf Christina,
Rothfelder Robin,
Scott Daniel J.,
Fischer Tillmann G.,
Zeitler Kirsten,
Wolf Robert
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002646
Subject(s) - phosphonium , reagent , chemistry , catalysis , alkylation , aryl , combinatorial chemistry , transition metal , white phosphorus , photocatalysis , organic synthesis , organic chemistry , phosphorus , alkyl
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.