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Chelation‐Assisted Cross‐Coupling of Anilines through In Situ Activation as Diazonium Salts with Boronic Acids under Ligand‐, Base‐, and Salt‐Free Conditions
Author(s) -
Joncour Roxan,
Susperregui Nicolas,
Pinaud Noël,
Miqueu Karinne,
Fouquet Eric,
Sotiropoulos JeanMarc,
Felpin FrançoisXavier
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300858
Subject(s) - transmetalation , chemistry , aryl , ligand (biochemistry) , salt (chemistry) , base (topology) , combinatorial chemistry , chelation , palladium , suzuki reaction , boronic acid , organic chemistry , catalysis , mathematical analysis , biochemistry , alkyl , receptor , mathematics
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, H 2 O, N 2 , and B(OH) 3 . The reaction mechanism has been deeply investigated through experimental and theoretical studies.