Chelation‐Assisted Cross‐Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand‐, Base‐, and Salt‐Free Conditions. Issue 28 (16th May 2013)

• Record Type: Journal Article
• Authors: Joncour, Roxan; Susperregui, Nicolas; Pinaud, Noël; Miqueu, Karinne; Fouquet, Eric; Sotiropoulos, Jean‐Marc; Felpin, François‐Xavier
• Is Part Of: Chemistry. Volume 19:Issue 28(2013)
• Page Start: 9291
• Page End: 9296
• Publication Date: 2013-05-16
• Subjects: aniline -- boronic acid -- cross‐coupling -- density functional calculations -- diazonium salt -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201300858
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 t BuOH, H2 O, N2, and B(OH)3 . The reaction mechanism has been deeply investigated through experimental and theoretical studies. Abstract : Eco‐couple : The cross‐coupling of anilines with aryl boronic acids has been achieved under ligand‐, base‐, and salt‐free conditions at room temperature (see scheme). The reaction mechanism, investigated through experimental and theoretical studies, proceeds through the formation of an aryl palladium alkoxo complex, which enables the transmetalation step without any external base, and gives only environmentally friendly byproducts.