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 (&gt; 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 pKa 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 was also used in a one-pot protocol to synthesize over twenty compounds containing all-carbon quaternary centers.

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

2019 Spring National Meeting

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