Metal‐Free Reduction of Phosphine Oxides, Sulfoxides, and N‐Oxides with Hydrosilanes using a Borinic Acid Precatalyst. Issue 24 (16th November 2017)

• Record Type: Journal Article
• Authors: Chardon, Aurélien; Maubert, Orianne; Rouden, Jacques; Blanchet, Jérôme
• Is Part Of: ChemCatChem. Volume 9:Issue 24(2017)
• Page Start: 4460
• Page End: 4464
• Publication Date: 2017-11-16
• Subjects: boron -- hydrosilanes -- oxides -- reaction mechanisms -- reduction; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201700986
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: The general reduction of phosphine oxides, sulfoxides, and amine N ‐oxides was achieved by combining bis(2‐chlorophenyl)borinic acid with phenylsilane. The reaction was shown to tolerate a wide range of substrates and could be performed under mild conditions, with only 2.5 mol % of the easily synthesized catalyst. Mechanistic investigations pointed to a key borohydride as the real catalyst and at bis(2‐chlorophenyl)borinic acid as a precatalyst. Abstract : Reduced to clear : The reduction of phosphine oxides, sulfoxides, and amine N ‐oxides is achieved by using bis(2‐chlorophenyl)borinic acid /phenylsilane. The reaction tolerates a wide range of substrates and can be performed under mild conditions with only a 2.5 mol % loading of the catalyst. NMR spectroscopy indicates that a borohydride is the key reducing species, and thus, bis(2‐chlorophenyl)borinic acid has to be considered a precatalyst.