Copper(I) Iodide-Tributyl Phosphite


[7681-65-4]  · CuI  · Copper(I) Iodide-Tributyl Phosphite  · (MW 190.45) (P(OBu)3)

[102-85-2]  · C12H27O3P  · Copper(I) Iodide-Tributyl Phosphite  · (MW 250.36)

(seldom used promoter of conjugate addition of alkyllithium reagents to a,b-unsaturated ketones)

Solubility: sol ether and THF.

Form Supplied in: reported to be generated in situ; not isolated in either case where use is reported; not commercially available.

Conjugate Addition.

A comparison of the Lithium Dimethylcuprate addition reaction to 5-methyl-2-cyclohexenone in the presence of copper(I) iodide-tributyl phosphite, Copper(I) Iodide-Trimethyl Phosphite, and Copper(I) Iodide-Tributylphosphine complexes, respectively, has been reported (eq 1).1 For the particular case in which the copper(I) iodide-tributyl phosphite was used, the reagent was generated in situ, the ratio of products in the mixture was not determined (although the overall yield was reported as 88%), and the authors point out that the trimethyl phosphite ester has proved to be a more satisfactory complexing agent … because of its volatility and partial water solubility.1 In the only other report,2 an n-butylcopper complex was added to 2-cyclopentenone, again in the presence of a variety of phosphine and phosphite complexing agents; in this case, miniscule yields of adduct were obtained when copper(I) iodide-tributyl phosphite was used.

Related Reagents.

Copper(I) Iodide-Tributylphosphine; Copper(I) Iodide-Triethylphosphine-Lithium Naphthalenide; Copper(I) Iodide-Triethyl Phosphite; Copper(I) Iodide-Trimethyl Phosphite; Lithium Diethylcuprate-Tributylphosphine.

1. House, H. O.; Fischer, W. F. JOC 1968, 33, 949.
2. Suzuki, M.; Suzuki, T.; Kawagishi, T.; Morita, Y.; Noyori, R. Isr. J. Chem. 1984, 24, 118.

Linda M. Mascavage

Beaver College, Glenside, PA, USA

David R. Dalton

Temple University, Philadelphia, PA, USA

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