[41962-55-4] · C6H5CuSe · Phenylselenocopper(I) · (MW 219.62)
(source of nucleophilic phenylselenide for preparation of lithium alkylphenylselenocuprates and organophosphinecopper(I) phenylselenolate complexes)
Physical Data: mp 150 °C (dec).
Solubility: partially sol cold THF.
Preparative Methods: phenylselenocopper can be prepared by two different procedures (eq 1). In the more straightforward procedure, Benzeneselenol is reacted with copper(I) oxide in ethanol at reflux to yield PhSeCu as a yellow or brown precipitate in 94% yield.1 Similarly, uncharacterized (PhSeCu)
Handling, Storage, and Precautions: selenium reagents should always be used in a fume hood.
Lithium alkyl(phenylseleno)cuprates, which are reacted with alkylseleno-substituted vinyl sulfones to effect stereoselective alkylation at the selenium-bearing carbon (eq 2), are prepared by the reaction of PhSeCu with the requisite alkyllithium in THF at 0 °C.1b The cuprates are generated in situ and then treated with the sulfone and warmed to rt.1b,4 Interestingly, these cuprates have afforded superior yields to the traditional cyano and thiophenyl mixed cuprates; the latter reagents also added in a conjugate fashion to give saturated products. Alkyl groups which have been coupled in good yield are Me, i-Pr, n-Bu, s-Bu, t-Bu, and 3-pentyl (67-97%).
A cyclohexylphosphinecopper(I) phenylselenolate complex has been synthesized from (PhSeCu)
William J. Hoekstra
The R. W. Johnson Pharmaceutical Research Institute, Spring House, PA, USA