Sterically Controlled Late-Stage C–H Alkynylation of Arenes

06 August 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

Alkynylation
C–H Activation
Dual-Ligand Catalysis
Palladium Catalysis
Late-Stage Modification

Supplementary materials

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Mondal et al Alkynylation SI
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