Sterically Controlled Late-Stage C–H Alkynylation of Arenes
- 12 November 2019
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 141 (47), 18662-18667
- https://doi.org/10.1021/jacs.9b10868
Abstract
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 Information
- Westf?lische Wilhelms-Universit?t M?nster
- Max-Planck-Gesellschaft
- Verband der Chemischen Industrie
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