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Phosphine-catalyzed vinylation at low acetylene pressure

The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-nbutylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of ac...

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Bibliographic Details
Main Authors: Sitte, Nikolai A. (Author) , Menche, Maximilian (Author) , Tužina, Pavel (Author) , Bienewald, Frank (Author) , Schäfer, Ansgar (Author) , Comba, Peter (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author) , Schaub, Thomas (Author)
Format: Article (Journal)
Language:English
Published: 2021
In: The journal of organic chemistry
Year: 2021, Volume: 86, Issue: 18, Pages: 13041-13055
ISSN:1520-6904
DOI:10.1021/acs.joc.1c01807
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.1c01807
Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/acs.joc.1c01807
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Author Notes:Nikolai A. Sitte, Maximilian Menche, Pavel Tužina, Frank Bienewald, Ansgar Schäfer, Peter Comba, Frank Rominger, A. Stephen K. Hashmi and Thomas Schaub
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Summary:The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-nbutylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
Item Description:Gesehen am 15.11.2021
Physical Description:Online Resource
ISSN:1520-6904
DOI:10.1021/acs.joc.1c01807

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