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Sterically Controlled Late-Stage C–H Alkynylation of Arenes

submitted on 05.08.2019, 16:50 and posted on 06.08.2019, 15:24 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.


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

Liebig Fellowship (Fonds der Chemischen Industrie)

WWU Münster


Email Address of Submitting Author


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



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no competing financial interests.