Oxidative α-C–C Bond Cleavage of 2° and 3° Alcohols to Aromatic Acids with O<sub>2</sub>at Room Temperature via Iron Photocatalysis
Zongnan Zhang, Guoxiang Zhang, Ni Xiong, Ting Xue, Junjie Zhang, Lu Bai, Qinyue Guo, Rong Zeng
Abstract
The selective α-C-C bond cleavage of unfunctionalized secondary (2°) and tertiary alcohols (3°) is essential for valorization of macromolecules and biopolymers. We developed a blue-light-driven iron catalysis for aerobic oxidation of 2° and 3° alcohols to acids via α-C-C bond cleavages at room temperature. The first example of oxygenation of the simple tertiary alcohols was reported. The iron catalyst and blue light play critical roles to enable the formation of highly reactive O radicals from alcohols and the consequent two α-C-C bond cleavages.
Topics & Concepts
ChemistryCatalysisPhotocatalysisRadicalBond cleavageTertiary alcoholsOrganic chemistryOxidative phosphorylationPhotochemistryCleavage (geology)Alcohol oxidationEngineeringFracture (geology)BiochemistryGeotechnical engineeringOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods