Direct access to π-extended phosphindolium salts by simple proton-induced cyclization of (o-alkynylphenyl)phosphanes
A detailed synthetic and mechanistic study for the synthesis of phosphindolium salts from easy accessible (o-alkynylphenyl)phosphanes is reported. Mechanistic investigation indicates a fast protonation at phosphorus as evidenced by the isolation of the phosphonium intermediate, followed by a protoph...
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| Main Authors: | , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
3 April 2017
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| In: |
Chemistry - a European journal
Year: 2017, Volume: 23, Issue: 23, Pages: 5429-5433 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700889 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201700889 Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/chem.201700889/abstract Verlag, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/chem.201700889/epdf 
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| Author Notes: | Sebastian Arndt, Max M. Hansmann, Frank Rominger, Matthias Rudolph, A. Stephen K. Hashmi |
| Summary: | A detailed synthetic and mechanistic study for the synthesis of phosphindolium salts from easy accessible (o-alkynylphenyl)phosphanes is reported. Mechanistic investigation indicates a fast protonation at phosphorus as evidenced by the isolation of the phosphonium intermediate, followed by a protophosphonylation reaction across the alkyne moiety. DFT calculations support our mechanistic proposal and indicate a reaction highly exergonic compared to our recently reported phosphinoauration. Photophysical measurements recorded fluorescence quantum yields up to 97 % in solution for the phosphindolium core and fluorescence was observed in the solid state. |
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| Item Description: | Im Titel ist pi als griechischer Buchstabe dargestellt Gesehen am 22.08.2017 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700889 |