Lithium (Z)-Bis(2-ethoxyvinyl)cuprate

Abstract

[64823-09-2] C8H14CuLiO2 (MW 212.71) InChI = 1S/2C4H7O.Cu.Li/c2*1-3-5-4-2;;/h2*1,3H,4H2,2H3;;/q;;-1;+1 InChIKey = NXGZSZVQFMMSBN-UHFFFAOYSA-N (a ‘lower order’ cuprate reagent, prepared in situ, which undergoes conjugate addition reactions and substitution reactions2) Solubility: sol THF. Preparative Methods: 1-Ethoxy-2-tributylstannylethylene is prepared by the hydrostannation of Ethoxyacetylene, which is then reacted with 1.1 equiv of n-Butyllithium in THF at −78 °C for 1 h to afford (Z)-2-Ethoxyvinyllithium. To this solution is added 0.5 equiv purified Copper(I) Iodide and 2.0 equiv Dimethyl Sulfide in THF. The mixture is stirred for 1 h, affording lithium bis(2-ethoxyvinyl)cuprate, a red-brown solution.2 Handling, Storage, and Precautions: air- and moisture-sensitive reagent prepared and used in situ. Use in a fume hood.