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Convergent Synthesis of Dihydrobenzofurans via Urea Ligand-Enabled Heteroannulation of 2-Bromophenols with 1,3-Dienes

Kaitlyn E. Houghtling, Amanda M. Canfield, Shauna M. Paradine

2022Organic Letters18 citationsDOIOpen Access PDF

Abstract

We disclose a palladium and urea ligand-mediated heteroannulation of 2-bromophenols and 1,3-dienes. This method addresses synthetic challenges present in the palladium-catalyzed heteroannulation of bifunctional reagents and olefins by engaging a diverse scope of coupling partners under a unified set of reaction conditions. Our recently developed urea ligand platform outperforms phosphine ligands to generate the dihydrobenzofuran motif in a convergent manner.

Topics & Concepts

ChemistryPhosphineBifunctionalUreaLigand (biochemistry)PalladiumCombinatorial chemistryReagentOrganic chemistryCatalysisReceptorBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis
Convergent Synthesis of Dihydrobenzofurans via Urea Ligand-Enabled Heteroannulation of 2-Bromophenols with 1,3-Dienes | Litcius