Copper-Catalyzed Homocoupling of Boronic Acids: A focus on B-to-Cu and Cu-to-Cu Transmetalations - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires Accéder directement au contenu
Pré-Publication, Document De Travail Année : 2022

Copper-Catalyzed Homocoupling of Boronic Acids: A focus on B-to-Cu and Cu-to-Cu Transmetalations

Aude Salamé
  • Fonction : Auteur
Jordan Rio
  • Fonction : Auteur
Ilaria Ciofini
Laurence Grimaud
Pierre-Adrien Payard

Résumé

Controlling and understanding Cu-catalyzed homocoupling reaction is crucial to prompt the development of efficient Cu-catalyzed cross-coupling reactions. The presence of a coordinating base (hydroxide, methoxide) enables the B-to-Cu(II) transmetalation from aryl boronic acid to CuIICl2 in methanol, through formation of a 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 a 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.

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Chimie
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Dates et versions

hal-03836058 , version 1 (01-11-2022)
hal-03836058 , version 2 (14-11-2022)

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Aude Salamé, Jordan Rio, Ilaria Ciofini, Lionel Perrin, Laurence Grimaud, et al.. Copper-Catalyzed Homocoupling of Boronic Acids: A focus on B-to-Cu and Cu-to-Cu Transmetalations. 2022. ⟨hal-03836058v1⟩
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