<br/><br/>Methylene cyclopropanes (MCPs) are useful synthetic intermediates in organic synthesis. Due to the strain in their structures, they are very reactive towards nucleophiles such as H2O, -CO2H, -SH, Cl-, and Br- However, there has not been any reported nucleophilic fluorination of MCPs to the best of our knowledge. This may be due to the weak nucleophilicity and low acidity of the existing hydrogen fluoride based reagents. We thus present the first nucleophilic fluorination of MCPs catalyzed by a Lewis acid using a novel nucleophilic reagent developed in the Hammond laboratory.

Synthesis of fluorinated homoallylic compounds via ring-opening nucleophilic fluorination of methylene cyclopropanes (MCP)

249th National Meeting (2015)

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