Table 3. Selective Cross-Coupling of 1e with Various Alkylsilicates^a.

^aUnless otherwise noted, reactions were performed using 1e (1.0 equiv, 0.5 mmol), 2 (1.2 equiv), NiCl₂·dme (2.5 mol %), Ru(bpy)₃(PF₆)₂ (2 mol %), and phen (5 mol %) in DMF (0.1 M) at rt for 24 h, irradiating with blue LEDs; ratios of 3:4 are indicated in parentheses, and these values were obtained before purification. All yields are isolated yields after purification.

^bValue in brackets denotes the yield when using the organic dye 4CzIPN (5 mol %) as the photocatalyst.

^cProduct obtained as the thioether rather than thiol from (3-mercaptopropyl)silicate.