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Sterically Controlled Late-Stage C–H Alkynylation of Arenes

preprint
submitted on 05.08.2019 and posted on 06.08.2019 by Arup Mondal, Hao Chen, Lea Flämig, Philipp Wedi, Manuel van Gemmeren
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 pre-functionalized 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.

Funding

Otto-Hahn-Award (Max-Planck-Society)

Liebig Fellowship (Fonds der Chemischen Industrie)

WWU Münster

History

Email Address of Submitting Author

mvangemmeren@uni-muenster.de

Institution

WWU Münster and Max-Planck-Institute for Chemical Energy Conversion

Country

Germany

ORCID For Submitting Author

0000-0003-3080-3579

Declaration of Conflict of Interest

The authors declare no competing financial interests.

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in Journal of the American Chemical Society

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