Copper Salt-Controlled Divergent Reactivity of [Cu]CF2 PO(OEt)2 with α-Diazocarbonyl Derivatives

Angew Chem Int Ed Engl. 2016 Nov 2;55(45):14141-14145. doi: 10.1002/anie.201608294. Epub 2016 Oct 10.

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-SCF2 PO(OEt)2 derivatives in good yields. Mechanistic studies were performed and suggested two different pathways to explain the formation of these products.

Keywords: copper; diazo compounds; fluorine; phosphate mimic; selective synthesis.

Publication types

  • Research Support, Non-U.S. Gov't