Site-selectivity in TBADT-photocatalyzed C(sp3)H functionalization of saturated alcohols and alkanes

Abstract

Site-selectivity in C(sp3)H functionalization of aliphatic alcohols and alkanes was studied using the decatungstate anion as a photocatalyst. In the case of aliphatic alcohols, CH bond a to the hydroxy group was preferentially functionalized. The a-site-selectivity is rationalized by polar effects imparted by the hydroxy group in the SH2 transition states. In contrast, CH functionalization of alkanes was largely affected by steric effects.