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- Title
Copper-Catalyzed Homocoupling of Boronic Acids: A Focus on B-to-Cu and Cu-to-Cu Transmetalations.
- Authors
Salamé, Aude; Rio, Jordan; Ciofini, Ilaria; Perrin, Lionel; Grimaud, Laurence; Payard, Pierre-Adrien
- Abstract
Controlling and understanding the Cu-catalyzed homocoupling reaction is crucial to prompt the development of efficient Cu-catalyzed cross-coupling reactions. The presence of a coordinating base (hydroxide and methoxide) enables the B-to-Cu(II) transmetalation from aryl boronic acid to CuIICl2 in methanol, through the formation of mixed Cu-(μ-OH)-B intermediates. A second B-to-Cu transmetalation to form bis-aryl Cu(II) complexes is disfavored. Instead, organocopper(II) dimers undergo a coupled transmetalation-electron transfer (TET) allowing the formation of bis-organocopper(III) complexes readily promoting reductive elimination. Based on this mechanism some guidelines are suggested to control the undesired formation of homocoupling product in Cu-catalyzed cross-coupling reactions.
- Subjects
BORONIC acids; DIMERS; CYCLIC voltammetry
- Publication
Molecules, 2022, Vol 27, Issue 21, p7517
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27217517