The role of acetylides in dual gold catalysis: a mechanistic investigation of the selectivity difference in the naphthalene synthesis from diynes
Under the conditions of dual activation catalysis with oxygen nucleophiles, β-substituted naphthalenes were obtained from 1,2-diethinyl arenes. Mechanistic studies, which include isotope labeling experiments, support that dual activation leads to β-substituted naphthalenes, whereas α-naphthalenes ar...
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| Hauptverfasser: | , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
8 January 2014
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| In: |
ChemCatChem
Year: 2014, Jahrgang: 6, Heft: 1, Pages: 199-204 |
| ISSN: | 1867-3899 |
| DOI: | 10.1002/cctc.201300820 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/cctc.201300820 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cctc.201300820 
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| Verfasserangaben: | Katharina Graf, Philip D. Hindenberg, Yusuke Tokimizu, Saori Naoe, Matthias Rudolph, Frank Rominger, Hiroaki Ohno, and A. Stephen K. Hashmi |
| Zusammenfassung: | Under the conditions of dual activation catalysis with oxygen nucleophiles, β-substituted naphthalenes were obtained from 1,2-diethinyl arenes. Mechanistic studies, which include isotope labeling experiments, support that dual activation leads to β-substituted naphthalenes, whereas α-naphthalenes are formed by π activation only, and no gold acetylide or dual activation is involved in the formation of the α-substituted products. Additional experiments on substrates that led to dibenzopentalenes support these mechanistic insights. |
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| Beschreibung: | Gesehen am 03.11.2020 |
| Beschreibung: | Online Resource |
| ISSN: | 1867-3899 |
| DOI: | 10.1002/cctc.201300820 |