Iridium-Catalyzed, Site-Selective Silylation of Secondary C(sp3)–H Bonds in Secondary Alcohols and Ketones

• DOI: 10.1021/jacs.3c03127
• Publication Date: 2023-08-28T14:38:26Z
• Authors: Jake W. Wilson; Bo Su; Makoto Yoritate; Jake X. Shi; John F. Hartwig
• Keywords: Reactivity

We report the iridium-catalyzed, stereoselective conversion of secondary alcohols or ketones to anti-1,3-diols by silylation C-H bonds γ oxygen and oxidation resulting oxasilolane. The in silyl ethers derived from is enabled a catalyst formed simple bisamidine ligand. occurs with high selectivity at bond over distal primary proximal bonds. Initial mechanistic investigations suggest that source newly achieved reactivity long lifetime binding constant strongly electron-donating