Site-selectivity in TBADT-photocatalyzed C(sp(3))-H Functionalization of Saturated Alcohols and Alkanes

Abstract

Site-selectivity in C(sp(3))-H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, C-H bond alpha to the hydroxy group was preferentially functionalized. The alpha-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the S(H)2 transition states. In contrast, C-H functionalization of alkanes was largely affected by steric effects.