Meta-Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

5 years ago

Meta-Selective C−H Arylation of Aromatic Alcohols with a Readily Attachable and Cleavable Molecular Scaffold

Eric M. Ferreira, Qiankun Li

The first example of meta-selective C−H arylations of arene alcohol-based substrates is described. The strategy involves the combination of the transient norbornene strategy with the quinoline-based acetal scaffold to achieve the formation of biaryl compounds. Both a two-step meta-arylation/scaffold cleavage process and a total telescoping procedure are described, highlighting the convenient attributes of attachment, removal, and recovery of the acetal scaffold. Moreover, the meta-arylated compounds can be further derivatized via ortho-selective functionalizations. These processes establish a foundation for catalytic polyfunctionalization of alcohol-based compounds. Getting Meta all the Time: The first example of meta-selective C−H arylations of arene alcohol-based substrates is described. The strategy involves the combination of the transient norbornene strategy with a quinolinyl acetal scaffold to achieve the formation of biaryl compounds. These processes establish a foundation for catalytic polyfunctionalization of alcohol-based compounds.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201703054