Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P, N) gold complexes. Issue 91 (30th October 2018)

• Record Type: Journal Article
• Authors: Tabey, Alexis; Berlande, Murielle; Hermange, Philippe; Fouquet, Eric
• Is Part Of: Chemical communications. Volume 54:Issue 91(2018)
• Page Start: 12867
• Page End: 12870
• Publication Date: 2018-10-30
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc07530a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Aryldiazonium salts and arylboronic acids were coupled via three different pathways from (P, N)–AuCl complexes, with enantiomeric excesses up to 26%. Abstract : In order to explore the different mechanisms possibly occurring in the Au-catalysed cross-coupling of ArN2 BF4 and ArB(OH)2 in the presence of CsF, various stoichiometric experiments were performed on gold complexes with (P, N) ligands. Employing 2-pyridylphenyl-diphenylphosphine allowed us to suggest three different mechanistic pathways, starting either with a transmetallation step, via two consecutive single electron transfers, or by implying a transmetallation between Au(i ) and Au(iii ) species. Moreover, when using commercially available chiral (P, N) ligands, the asymmetric formation of atropoisomeric biaryls from suitable aryldiazonium salts and arylboronic acids could be achieved with e.e. up to 26%.