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High chemoselectivity in the phenol synthesis

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Author(s): Matthias Rudolph | Melissa Q. McCreery | Wolfgang Frey | A. Stephen K. Hashmi

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 7;
Issue: 1;
Start page: 794;
Date: 2011;
Original page

Keywords: alcohols | alkenes | alkynes | furans | gold | ketones

ABSTRACT
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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