Ruthenium-Catalyzed C−H Bond Alkylation of Arylphosphine Oxides with Alkenes: A Straightforward Access to Bifunctional Phosphorous Ligands with a Pendent Carboxylate

C.-S. Wang (1) , Pierre H. Dixneuf (1) , Jean-François Soulé (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

An efficient approach for the fast modification of arylphosphine oxides involving ruthenium(II)-catalyzed C−H bond alkylation with functional alkenes versus alkenylation has been developed depending on the acidic reaction conditions. Using this methodology, a few examples of desymmetrization of diarylphosphine oxides has allowed the formation of phosphorus derivatives containing three different substituents. After reduction of the phosphine oxide, this method allows the formation of aryl phosphines bearing a flexible pendent carboxylate.

Keywords: ruthenium(II); aryl phosphine oxides; alkylation; C−H bond activation; bifunctional phosphine ligands

Domains: Chemical Sciences; Chemical Sciences; Catalysis

C.-S. Wang, Pierre H. Dixneuf, Jean-François Soulé. Ruthenium-Catalyzed C−H Bond Alkylation of Arylphosphine Oxides with Alkenes: A Straightforward Access to Bifunctional Phosphorous Ligands with a Pendent Carboxylate. ChemCatChem, 2017, 9 (16), pp.3117--3120. ⟨10.1002/cctc.201700557⟩. ⟨hal-01581227⟩