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CC BY-ND-NC 4.0 · Synthesis 2018; 50(10): 2019-2026
DOI: 10.1055/s-0037-1609435
DOI: 10.1055/s-0037-1609435
paper
Selective Substitution of POCl3 with Organometallic Reagents: Synthesis of Phosphinates and Phosphonates
The research leading to these results received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 Research and Innovation Program: Grant Agreement 694078 – Solvometallurgy for critical metals (SOLCRIMET).Weitere Informationen
Publikationsverlauf
Received: 07. Februar 2018
Accepted after revision: 27. Februar 2018
Publikationsdatum:
05. April 2018 (online)
Abstract
The selectivity of the substitution reaction of phosphoryl chloride with organometallic reagents was investigated using NMR spectroscopy. This led to the discovery that the selectivity of the substitution reaction can be tuned by choosing a proper organometallic reagent. A phosphinate could be obtained by using a Grignard reagent whereas an organozinc reagent provided a phosphonate. Based on these results, one-pot synthetic methods for the preparation of phosphinates and phosphonates using commercially available starting materials were developed. Both methods allow the synthesis of a broad range of either phosphinate or phosphonate derivatives in a straightforward and general procedure. Moreover, using these one-pot procedures, mixed systems substituted with different alkyl/aryl groups can be prepared.
Key words
selectivity - substitution - phosphoryl chloride - phosphinate - phosphonate - Grignard reagent - organozinc reagentSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609435.
- Supporting Information
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