Synthesis of Symmetrical and Unsymmetrical 1,3-Diheteroarylbenzenes Through Palladium-Catalyzed Direct Arylation of Benzene-1,3-disulfonyl Dichloride and 3-Bromobenzenesulfonyl Chlorides

Imane Idris (1, 2) , Fazia Derridj (2, 3, 1) , Safia Djebbar (3) , Jean-François Soulé (2) , Henri Doucet (2)

1 LCAGC - Laboratoire de Chimie appliquée & génie chimique [Tizi-Ouzou]
2 ISCR - Institut des Sciences Chimiques de Rennes
3 LHCIM - Laboratoire d'hydrométallurgie et chimie inorganique moléculaire

The palladium-catalyzed synthesis of unsymmetrical 1,3-diheteroarylbenzenes was investigated. The first synthetic pathway relies on the desymmetrization of benzene-1,3-disulfonyl dichloride through two successive palladium-catalyzed direct desulfitative arylations with two different heteroarenes. The second strategy employs the orthogonal functionalization of 3-bromobenzenesulfonylchloride using an iterative C–H bond arylation sequence, namely, palladium-catalyzed direct desulfitative arylation followed by a palladium-catalyzed direct arylation step using aryl bromide as the coupling partner. The synthesis of symmetrical 1,3-diheteroarylbenzenes was also investigated

Keywords: Catalysis; C–H Arylation; Desulfitative; palladium; Tridentate Ligand

Domains: Chemical Sciences; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry

Imane Idris, Fazia Derridj, Safia Djebbar, Jean-François Soulé, Henri Doucet. Synthesis of Symmetrical and Unsymmetrical 1,3-Diheteroarylbenzenes Through Palladium-Catalyzed Direct Arylation of Benzene-1,3-disulfonyl Dichloride and 3-Bromobenzenesulfonyl Chlorides. Tetrahedron, 2015, 71 (52), pp.9617-9625. ⟨10.1016/j.tet.2015.10.082⟩. ⟨hal-01224511⟩