Expanding the Clip-and-Cleave Concept: Approaching Enantioselective C-H Hydroxylations by Copper Imine Complexes Using O₂ and H₂O₂ as Oxidants.

ABSTRACT: Copper-mediated aromatic and aliphatic C-H hydroxylations using benign oxidants (O₂ and H₂O₂) have been studied intensively in recent years to meet the growing demand for efficient and green C-H functionalizations. Herein, we report an enantioselective variant of the so-called clip-and-cleave concept for intramolecular ligand hydroxylations by the application of chiral diamines as directing groups. We tested the hydroxylation of cyclohexanone and 1-acetyladamantane under different oxidative conditions (Cu^I/O₂; Cu^I/H₂O₂; Cu^II/H₂O₂) in various solvents. As an outstanding example, we obtained (R)-1-acetyl-2-adamantol with a yield of 37% and >99:1 enantiomeric excess

SUBMITTER: Petrillo A 

PROVIDER: S-EPMC11823439 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature