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

Simple item page
dc.citation.firstpage7992en_US
dc.citation.journalTitleChemical Scienceen_US
dc.citation.lastpage7999en_US
dc.citation.volumeNumber9en_US
dc.contributor.authorLovato, Kaitlynen_US
dc.contributor.authorGuo, Lirongen_US
dc.contributor.authorXu, Qing-Longen_US
dc.contributor.authorLiu, Fengtingen_US
dc.contributor.authorYousufuddin, Muhammeden_US
dc.contributor.authorEss, Daniel H.en_US
dc.contributor.authorKürti, Lászlóen_US
dc.contributor.authorGao, Hongyinen_US
dc.date.accessioned2019-01-08T15:37:44Zen_US
dc.date.available2019-01-08T15:37:44Zen_US
dc.date.issued2018en_US
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.en_US
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.en_US
dc.identifier.digitalc8sc02758gen_US
dc.identifier.doihttps://doi.org/10.1039/c8sc02758gen_US
dc.identifier.urihttps://hdl.handle.net/1911/104978en_US
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.rightsThis Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licenceen_US
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/en_US
dc.titleTransition metal-free direct dehydrogenative arylation of activated C(sp3)–H bonds: synthetic ambit and DFT reactivity predictionsen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpublisher versionen_US
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
c8sc02758g.pdf
Size:
2.51 MB
Format:
Adobe Portable Document Format
Download
Collections
Faculty Publications
Chemistry Publications