Fig. 2: Substrate scope of aryl iodides, including late-stage functionalization of bioactive compounds.
From: Direct deoxygenative arylation of saccharides via phosphorus-assisted C−OH bond activation
Reaction conditions: 1a (0.1 mmol, 1.0 equiv.), 2 (0.2 mmol, 2.0 equiv.), NiCl2.dtbbpy (0.01 mmol, 10 mol%), ClPPh2 (0.11 mmol, 1.1 equiv.), DMAP (0.01 mmol, 10 mol%), and Cy2NH (0.12 mmol, 1.2 equiv.) in 1,4-dioxane (0.25 mL, 0.4 M) at room temperature for 20 min; then Zn (0.3 mmol, 3.0 equiv.), I2 (0.1 mmol, 1.0 equiv.) at room temperature for 18 h. Isolated yields are reported; All products observed and isolated occur as single anomer. Bn benzyl, dtbbpy 4,4’-di-tert-butyl-2,2’-dipyridyl; DMAP 4-dimethylaminopyridine, Cy cyclohexyl, Me methyl, Ac acetyl.
