High chemoselectivity in the phenol synthesis

Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of the gold-catalyzed phenol synthesis are much...

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Hauptverfasser: Rudolph, Matthias (VerfasserIn) , McCreery, Melissa Q. (VerfasserIn) , Frey, Wolfgang (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 10 Jun 2011
In: Beilstein journal of organic chemistry
Year: 2011, Jahrgang: 7, Pages: 794-801
ISSN:1860-5397
DOI:10.3762/bjoc.7.90
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.3762/bjoc.7.90
Verlag, lizenzpflichtig, Volltext: https://www.beilstein-journals.org/bjoc/articles/7/90
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Verfasserangaben:Matthias Rudolph, Melissa Q. McCreery, Wolfgang Frey and A. Stephen K. Hashmi

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520 |a Efforts to trap early intermediates of the gold-catalyzed phenol synthesis failed. Neither inter- nor intramolecularly offered vinyl groups, ketones or alcohols were able to intercept the gold carbenoid species. This indicates that the competing steps of the gold-catalyzed phenol synthesis are much faster than the steps of the interception reaction. In the latter the barrier of activation is higher. At the same time this explains the high tolerance of this very efficient and general reaction towards functional groups. 
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