A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones.

ABSTRACT: Advances in site-selective functionalization reactions have enabled single atom changes on the periphery of a complex molecule, but reaction manifolds that enable such changes on the core framework of the molecule remain sparse. Here, we disclose a strategy for carbon-to-oxygen substitution in cyclic diarylmethanes and diarylketones to yield cyclic diarylethers. Oxygen atom insertion is accomplished by methylene and Baeyer-Villiger oxidations. To remove the carbon atom in this C-to-O "atom swap" process, we developed a nickel-catalyzed decarbonylation of lactones to yield the corresponding cyclic diaryl ethers. This reaction was enabled by mechanistic studies with stoichiometric nickel(ii) complexes that led to the optimization of a ligand capable of promoting a challenging C(sp²

SUBMITTER: Luu QH 

PROVIDER: S-EPMC8790783 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature