Transition metal-free direct dehydrogenative arylation of activated C(sp³)-H bonds: synthetic ambit and DFT reactivity predictions.

ABSTRACT: A transition metal-free dehydrogenative method for the direct mono-arylation of a wide range of activated C(sp³)-H bonds has been developed. This operationally simple and environmentally friendly aerobic arylation uses tert-BuOK as the base and nitroarenes as electrophiles to prepare up to gram quantities of structurally diverse sets (>60 examples) of α-arylated esters, amides, nitriles, sulfones and triaryl methanes. DFT calculations provided a predictive model, which states that substrates containing a C(sp³)-H bond with a sufficiently low pK _a value should readily undergo arylation. The DFT prediction was confirmed through experimental testing of nearly a dozen substrates containing activated C(sp³)-H bonds. This arylation method

SUBMITTER: Lovato K 

PROVIDER: S-EPMC6202766 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature