Selective Suzuki-Miyaura monocouplings with symmetrical dibromoarenes and aryl ditriflates for the one-pot synthesis of unsymmetrical triaryls

C. Minard (1) , C. Palacio (1) , K. Cariou (1) , Robert H Dodd (1)

1 ICSN - Institut de Chimie des Substances Naturelles

The various parameters that would permit achievement of selective Suzuki-Miyaura mono-couplings on symmetrical dihaloarenes were studied. Using operationally simple conditions and widely available reagents high selectivity and efficiency can be obtained for a broad range of substrates. The 38 different examples described provide a valuable toolbox for rapid access to unsymmetrical triaryls, as illustrated by the preparation of diarylpyridine 8, terphenyl 9 and diarylpyrrole 10.

Mots clés: Suzuki-Miyaura; selective coupling; potassium trifluoroborates; triaryls

Domaines: Chimie organique

C. Minard, C. Palacio, K. Cariou, Robert H Dodd. Selective Suzuki-Miyaura monocouplings with symmetrical dibromoarenes and aryl ditriflates for the one-pot synthesis of unsymmetrical triaryls. European Journal of Organic Chemistry, 2014, 2014 (14), pp.2942-2955. ⟨10.1002/ejoc.201400090⟩. ⟨hal-00994366⟩