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Hydroxymethyl as Directing Group for the Regioselective Palladium-Catalyzed C–H Bond C2-Arylation of a C3-Substituted Furan

Year: 2025

Type: article

Abstract: The reaction outcome of the palladium-catalyzed C–H arylation of 3-(hydroxymethyl)furan was investigated. The hydroxymethyl group at the C3 position of the furan proved to be a powerful directing group for controlling regioselective direct arylation at the C2 position, while the C5-position and the hydroxymethyl function of the furan ring remained unaffected. The reaction tolerates a very wide variety of electron-poor or rich aryl bromides, bearing substituents at the para- or meta-positions, as well as heteroaryl bromides. It should be noted that, for this coupling reaction, an air-stable palladium catalyst and an inexpensive base were used. Using an excess of specific aryl bromides, 3-(hydroxymethyl)furan can also be diarylated at positions 2 and 5.

Source: Synthesis

DOI: 10.1055/s-0043-1773515

Authors: Ridha Salem, Henri Doucet, Rabeb Ben Romdhane, Norman Le Floch

Institutions: University of Sfax, Faculty of Sciences of Sfax, Université de Rennes

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche

OpenAlex ID: W4408466609

FWCI:

Cites: 43

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Related to: 10