Copper Salt-Controlled Divergent Reactivity of [Cu]CF PO(OEt) with α-Diazocarbonyl Derivatives.

Angew Chem Int Ed Engl

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.

Published: November 2016

AI Article Synopsis

  • Researchers discovered that changing the copper salt used in reactions with α-diazocarbonyl compounds can significantly alter the outcome of the reaction.
  • This method allows for the efficient production of two different types of compounds—(Z)-α-fluorovinylphosphonate and alkyl-SCF PO(OEt) derivatives—just by altering the copper counteranion.
  • Mechanistic studies indicate that two distinct paths are involved in the formation of these products, helping to explain the different reactivities observed.

Article Abstract

Herein, we report a copper salt-controlled divergent reactivity toward α-diazocarbonyl compounds. By a simple change of the copper counteranion under identical reaction conditions, the reported method allowed an easy access to either (Z)-α-fluorovinylphosphonate or alkyl-SCF PO(OEt) derivatives in good yields. Mechanistic studies were performed and suggested two different pathways to explain the formation of these products.

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http://dx.doi.org/10.1002/anie.201608294DOI Listing

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Copper Salt-Controlled Divergent Reactivity of [Cu]CF PO(OEt) with α-Diazocarbonyl Derivatives.

Angew Chem Int Ed Engl

November 2016

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.

Article Synopsis
  • Researchers discovered that changing the copper salt used in reactions with α-diazocarbonyl compounds can significantly alter the outcome of the reaction.
  • This method allows for the efficient production of two different types of compounds—(Z)-α-fluorovinylphosphonate and alkyl-SCF PO(OEt) derivatives—just by altering the copper counteranion.
  • Mechanistic studies indicate that two distinct paths are involved in the formation of these products, helping to explain the different reactivities observed.
View Article and Find Full Text PDF

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