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Different selectivities in the insertions into C(sp2)-H bonds: Benzofulvenes by dual Gold catalysis competition experiments

An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)-H bond insertion in easily available starting materials. The insertion takes place with an excl...

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Hauptverfasser: Plajer, Alex (VerfasserIn) , Ahrens, Lukas (VerfasserIn) , Wieteck, Marcel (VerfasserIn) , Lustosa, Danilo Machado (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: July 25, 2018
In: Chemistry - a European journal
Year: 2018, Jahrgang: 24, Heft: 42, Pages: 10766-10772
ISSN:1521-3765
DOI:10.1002/chem.201801031
Online-Zugang:Resolving-System, Volltext: http://dx.doi.org/10.1002/chem.201801031
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201801031
Volltext
Verfasserangaben:Alex J. Plajer, Lukas Ahrens, Marcel Wieteck, Danilo M. Lustosa, Rasool Babaahmadi, Brian Yates, Alireza Ariafard, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp2)-H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C-H positions. A bidirectional synthesis with two competing ortho-aryl C-H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C-H bonds with a benzylic methyl group also showed perfect selectivity.
Beschreibung:Im Titel ist die Ziffer 2 hochgestellt
Gesehen am 11.12.2018
Beschreibung:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201801031

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