Reactivity of 3-Bromofuran in Pd-Catalyzed C–H Bond Arylation toward the Synthesis of 2,3,5-Triarylfurans

Arpan Sasmal; Thierry Roisnel; Jitendra K. Bera; Henri Doucet; Jean-François Soulé

doi:10.1055/s-0037-1611819

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(17): 3241-3249
DOI: 10.1055/s-0037-1611819

paper

Reactivity of 3-Bromofuran in Pd-Catalyzed C–H Bond Arylation toward the Synthesis of 2,3,5-Triarylfurans

Arpan Sasmal

^aUniv Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France eMail: Henri.doucet@univ-rennes1.fr eMail: jean-francois.soule@univ-rennes1.fr

,

Thierry Roisnel

^aUniv Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France eMail: Henri.doucet@univ-rennes1.fr eMail: jean-francois.soule@univ-rennes1.fr

,

Jitendra K. Bera

^bDepartment of Chemistry and Center for Environmental Science and Engineering, Indian Institute of Technology Kanpur, Kanpur 208016, India

,

Henri Doucet*

^aUniv Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France eMail: Henri.doucet@univ-rennes1.fr eMail: jean-francois.soule@univ-rennes1.fr

,

Jean-François Soulé *

^aUniv Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France eMail: Henri.doucet@univ-rennes1.fr eMail: jean-francois.soule@univ-rennes1.fr

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Abstract

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Abstract

Arylation of the C–H bond at the C2 position of 3-bromofuran is achieved using aryl bromides as coupling partners in the presence of phosphine-free Pd(OAc)₂/KOAc in DMA. This procedure gives C2,C5-di- and even C2,C4,C5-triarylated 3-bromofuran derivatives when larger amounts of aryl bromides are employed. In addition, C2,C3,C5-triarylated furans—containing three different aryl groups—are synthesized via a C2–H bond arylation/Suzuki reaction/C5–H bond arylation sequence.

Key words

palladium - furans - C–H bond arylation - aryl bromides

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Referenzen

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