Chelation-assisted cross-coupling of anilines through in situ activation as diazonium salts with boronic acids under ligand-, base-, and salt-free conditions

R. Joncour (1) , Nicolas Susperregui , N. Pinaud , Karinne Miqueu (2) , E. Fouquet , Jean-Marc Sotiropoulos (3) , F.-X. Felpin (4)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
3 IPREM - Institut pluridisciplinaire de recherche sur l'environnement et les matériaux
4 LSOHOOM - Laboratoire de Synthèse Organique (Hétérochimie organique, organoéléments et matériaux)

We describe the coupling of anilines with aryl boronic acids, under ligand-, base-, and salt-free conditions at room temperature. This new reaction proceeds through the formation of an aryl palladium alkoxo complex, which allows the transmetalation step with aryl boronic acids without any external base. Importantly, this sustainable procedure generates only environmentally friendly byproducts such as tBuOH, H2O, N2, and B(OH)3. The reaction mechanism has been deeply investigated through experimental and theoretical studies. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Domaines: Catalyse; Chimie de coordination; Chimie organique; Polymères; Chimie théorique et/ou physique

R. Joncour, Nicolas Susperregui, N. Pinaud, Karinne Miqueu, E. Fouquet, et al.. Chelation-assisted cross-coupling of anilines through in situ activation as diazonium salts with boronic acids under ligand-, base-, and salt-free conditions. Chemistry - A European Journal, 2013, 19 (28), pp.9291-9296. ⟨10.1002/chem.201300858⟩. ⟨hal-01613226⟩