Light-induced gold-catalyzed Hiyama arylation: a coupling access to biarylboronates
Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis o...
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| Hauptverfasser: | , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
09 October 2018
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| In: |
Angewandte Chemie. International edition
Year: 2018, Jahrgang: 57, Heft: 51, Pages: 16648-16653 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201806427 |
| Online-Zugang: | Resolving-System, Volltext: http://dx.doi.org/10.1002/anie.201806427 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201806427 
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| Verfasserangaben: | Jin Xie, Kohei Sekine, Sina Witzel, Petra Krämer, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi |
| Zusammenfassung: | Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C−X (heteroatom) and C−C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis. |
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| Beschreibung: | Gesehen am 05.02.2019 |
| Beschreibung: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.201806427 |