Rothfelder, Robin and Streitferdt, Verena and Lennert, Ulrich and Cammarata, Jose and Scott, Daniel J. and Zeitler, Kirsten and Gschwind, Ruth M. and Wolf, Robert (2021) Photocatalytic Arylation of P-4 and PH3: Reaction Development Through Mechanistic Insight. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 60 (46). pp. 24650-24658. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
Detailed P-31{H-1} NMR spectroscopic investigations provide deeper insight into the complex, multi-step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P-4). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non-innocent behavior of the commonly employed terminal reductant Et3N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)(2)][PF6] (dtbbpy=4,4 '-di-tert-butyl-2,2 '-bipyridine) and 3DPAFIPN. Inspired by the observation of PH3 as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P-4 arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | WHITE PHOSPHORUS; ACTIVATION; FUNCTIONALIZATION; DEPROTONATION; ROUTE; arylation; NMR spectroscopy; phosphine; photoredox catalysis; white phosphorus |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie > Arbeitskreis Prof. Dr. Robert Wolf Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Ruth Gschwind |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 07 Jul 2022 04:33 |
| Last Modified: | 07 Jul 2022 04:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/45802 |
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