6533b7d0fe1ef96bd125a3dd

RESEARCH PRODUCT

Metal- and Reagent-Free Anodic C−C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis

Siegfried R. WaldvogelRobert FrankeBernardo A. Frontana-uribeBernardo A. Frontana-uribeMaurice DörrDieter SchollmeyerSebastian Lips

subject

010405 organic chemistryOrganic ChemistryGeneral Chemistry010402 general chemistryElectrochemistryMetathesis01 natural sciencesCombinatorial chemistryCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryFuranReagentMoietyPhenolPhenolsBenzofuran

description

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.

https://doi.org/10.1002/chem.201800919