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  Sterically Controlled Late-Stage C-H Alkynylation of Arenes

Mondal, A., Chen, H., Flämig, L., Wedi, P., & van Gemmeren, M. (2019). Sterically Controlled Late-Stage C-H Alkynylation of Arenes. Journal of the American Chemical Society, 141(47), 18662-18667. doi:10.1021/jacs.9b10868.

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 Urheber:
Mondal, Arup1, Autor           
Chen, Hao1, Autor           
Flämig, Lea, Autor
Wedi, Philipp1, Autor           
van Gemmeren, Manuel1, Autor           
Affiliations:
1Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society, ou_3023874              

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 Zusammenfassung: Phenylacetylenes are key structural motifs in organic chemistry, which find widespread applications in bioactive molecules, synthetic intermediates, functional materials, and reagents. These molecules are typically prepared from prefunctionalized starting materials, e.g. using the Sonogashira coupling, or using directing group-based C-H activation strategies. While highly efficient, these approaches remain limited by their inherent selectivities for specific regioisomers. Herein we present a complementary approach based on an arene-limited nondirected C-H activation. The reaction is predominantly controlled by steric rather than electronic factors and thereby gives access to a complementary product spectrum with respect to traditional methods. A broad scope as well as the suitability of this protocol for late-stage functionalization are demonstrated.

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 Datum: 2019
 Publikationsstatus: Erschienen
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 Ort, Verlag, Ausgabe: -
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 Identifikatoren: ISI: 000500418700005
DOI: 10.1021/jacs.9b10868
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Titel: Journal of the American Chemical Society
  Andere : JACS
  Kurztitel : J. Am. Chem. Soc.
Genre der Quelle: Zeitschrift
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Ort, Verlag, Ausgabe: Washington, DC : American Chemical Society
Seiten: - Band / Heft: 141 (47) Artikelnummer: - Start- / Endseite: 18662 - 18667 Identifikator: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870