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

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dc.citation.firstpage7992
dc.citation.journalTitleChemical Science
dc.citation.lastpage7999
dc.citation.volumeNumber9
dc.contributor.authorLovato, Kaitlyn
dc.contributor.authorGuo, Lirong
dc.contributor.authorXu, Qing-Long
dc.contributor.authorLiu, Fengting
dc.contributor.authorYousufuddin, Muhammed
dc.contributor.authorEss, Daniel H.
dc.contributor.authorKürti, László
dc.contributor.authorGao, Hongyin
dc.date.accessioned2019-01-08T15:37:44Z
dc.date.available2019-01-08T15:37:44Z
dc.date.issued2018
dc.description.abstractA 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 was also used in a one-pot protocol to synthesize over twenty compounds containing all-carbon quaternary centers.
dc.identifier.citationLovato, Kaitlyn, Guo, Lirong, Xu, Qing-Long, et al.. "Transition metal-free direct dehydrogenative arylation of activated C(sp3)–H bonds: synthetic ambit and DFT reactivity predictions." <i>Chemical Science,</i> 9, (2018) Royal Society of Chemistry: 7992-7999. https://doi.org/10.1039/c8sc02758g.
dc.identifier.digitalc8sc02758g
dc.identifier.doihttps://doi.org/10.1039/c8sc02758g
dc.identifier.urihttps://hdl.handle.net/1911/104978
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.rightsThis Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/
dc.titleTransition metal-free direct dehydrogenative arylation of activated C(sp3)–H bonds: synthetic ambit and DFT reactivity predictions
dc.typeJournal article
dc.type.dcmiText
dc.type.publicationpublisher version
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