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Metal‐ and Reagent‐Free Anodic C−C Cross‐Coupling of Phenols with Benzofurans leading to a Furan Metathesis
Author(s) -
Lips Sebastian,
FrontanaUribe Bernardo Antonio,
Dörr Maurice,
Schollmeyer Dieter,
Franke Robert,
Waldvogel Siegfried R.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800919
Subject(s) - benzofuran , moiety , reagent , metathesis , furan , chemistry , salt metathesis reaction , combinatorial chemistry , organic chemistry , polymerization , polymer
Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal‐ and reagent‐free, electrosynthetic, and highly efficient method, that allows access to (2‐hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C−C cross‐coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single‐step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.