Synthesis 2017; 49(02): 252-259
DOI: 10.1055/s-0036-1588610
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© Georg Thieme Verlag Stuttgart · New York

Electro-organic Synthesis as a Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols

Barbara Riehl
a  Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
,
Katrin M. Dyballa
b  Evonik Performance Materials GmbH, Paul-Baumann-Straße 1, 45772 Marl, Germany
,
Robert Franke
b  Evonik Performance Materials GmbH, Paul-Baumann-Straße 1, 45772 Marl, Germany
c  Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum, Germany   Email: waldvogel@uni-mainz.de
,
Siegfried R. Waldvogel*
a  Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
› Author Affiliations
Further Information

Publication History

Received: 30 July 2016

Accepted after revision: 07 September 2016

Publication Date:
18 October 2016 (online)

Dedicated to D. Enders on the occasion of his 70th birthday

Abstract

The dehydrogenative cross-coupling of phenols and naphthols can be achieved by several oxidative methods. However, the key is the use of fluorinated alcohols such as 1,1,1,3,3,3-hexafluoroisopropanol. The direct application of electricity represents an alternative synthetic approach, which is superior to other oxidizers (e.g., peroxides). The method is sustainable, inherently safe, and easily scalable.

Supporting Information

 
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