Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans

Anissa Beladhria; Kedong Yuan; Hamed Ben Ammar; Jean-Francois Soulé; Ridha Ben Salem; Henri Doucet

doi:10.1055/s-0033-1340188

Synthesis, Table of Contents

Synthesis 2014; 46(18): 2515-2523
DOI: 10.1055/s-0033-1340188

paper

Benzenesulfonyl Chlorides: Alternative Coupling Partners for Regiocontrolled Palladium-Catalyzed Direct Desulfitative 5-Arylation of Furans

Anissa Beladhria

^aInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 ‘Organométalliques, Matériaux et Catalyse’, Campus de Beaulieu, 35042 Rennes, France Fax: +33(223)236939 Email: henri.doucet@univ-rennes1.fr

^bLaboratoire de Chimie Organique Physique (UR 11ES74) Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, Tunisie

,

Kedong Yuan

^aInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 ‘Organométalliques, Matériaux et Catalyse’, Campus de Beaulieu, 35042 Rennes, France Fax: +33(223)236939 Email: henri.doucet@univ-rennes1.fr

,

Hamed Ben Ammar

^cLaboratoire de Synthèse Asymétrique et Catalyse Homogène, (UR 11ES56) Université de Monastir, Faculté des Sciences de Monastir, avenue de l’environnement, Monastir 5000, Tunisie

,

Jean-Francois Soulé

^aInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 ‘Organométalliques, Matériaux et Catalyse’, Campus de Beaulieu, 35042 Rennes, France Fax: +33(223)236939 Email: henri.doucet@univ-rennes1.fr

,

Ridha Ben Salem*

^bLaboratoire de Chimie Organique Physique (UR 11ES74) Université de Sfax, Faculté des Sciences de Sfax, Route de la Soukra km 4, 3038 Sfax, Tunisie

,

Henri Doucet*

^aInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1 ‘Organométalliques, Matériaux et Catalyse’, Campus de Beaulieu, 35042 Rennes, France Fax: +33(223)236939 Email: henri.doucet@univ-rennes1.fr

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Abstract

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Abstract

The reactivity of furan derivatives in palladium-catalyzed desulfitative arylation was studied. Alkyl-substituted furan derivatives were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst; regioselective arylation at C5 of the furan was observed in all cases. This reaction tolerates a wide variety of substituents on the benzenesulfonyl derivative. It should be noted that even bromo- and iodobenzenesulfonyl chlorides were successfully coupled with furan derivatives without cleavage of the C–Br or C–I bonds, thus allowing further transformations. The use of these reactants demonstrates the potential of benzenesulfonyl chlorides as coupling partners to access to functionalized 5-arylfurans.

Key words

palladium - C–H bond activation - furans - benzenesulfonyl chlorides - arylation

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References

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