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Issue 41, 2018
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Transition metal-free direct dehydrogenative arylation of activated C(sp3)–H bonds: synthetic ambit and DFT reactivity predictions

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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 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.

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

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Publication details

The article was received on 22 Jun 2018, accepted on 23 Aug 2018 and first published on 27 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC02758G
Citation: Chem. Sci., 2018,9, 7992-7999
  • Open access: Creative Commons BY license
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    Transition metal-free direct dehydrogenative arylation of activated C(sp3)–H bonds: synthetic ambit and DFT reactivity predictions

    K. Lovato, L. Guo, Q. Xu, F. Liu, M. Yousufuddin, D. H. Ess, L. Kürti and H. Gao, Chem. Sci., 2018, 9, 7992
    DOI: 10.1039/C8SC02758G

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