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Palladium-Catalyzed Cross-Coupling of <i>gem-</i>Difluorocyclopropanes with <i>gem</i>-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes

Ebrahim‐Alkhalil M. A. Ahmed, Hongchen Zhang, Wen-Gen Cao, Tian‐Jun Gong

2023Organic Letters34 citationsDOI

Abstract

This study presents a novel method for the regioselective coupling of gem -difluorinated cyclopropanes with gem -diborylmethane, utilizing a Pd-catalyst system. This innovative approach enables the synthesis of 2-fluoroalkenyl monoboronate scaffolds with high Z -selectivity. The resulting products undergo further transformations, including oxidation, Suzuki cross-coupling, and trifluoroborylation, all of which are achieved with good yields. This work introduces a valuable synthetic pathway to access important fluorinated compounds for various applications in organic chemistry.

Topics & Concepts

ChemistryRegioselectivityCatalysisPalladiumCoupling (piping)Combinatorial chemistrySelectivityOrganic synthesisOrganic chemistryEngineeringMechanical engineeringFluorine in Organic ChemistryOrganoboron and organosilicon chemistry
Palladium-Catalyzed Cross-Coupling of <i>gem-</i>Difluorocyclopropanes with <i>gem</i>-Diborylalkanes for the Synthesis of Boryl-Substituted Fluorinated Alkenes | Litcius