Cross-coupling of organic compounds using cuprous iodide

Details Cross-coupling of organic compounds using cuprous iodide Cross-coupling of organic compounds using cuprous iodide

1996-08-22

1998-12-22

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

560 54, 560126, 560174, 560205, 568309, 568319, 568346, 568348, 568397, 568398, 568412, C07C 6976

Patent

active

058522000

ABSTRACT:
Cross-coupling or addition reactions of organic compounds, including acid halides, allylic halides, and .alpha.,.beta.-unsaturated carbonyl containing compounds, with organozinc compounds may be readily and safely carried out in the presence of cuprous iodide. The use of this catalyst in the coupling reaction provides for the preparation of commercially useful products in the pharmaceutical, agrochemical and other industries.

REFERENCES:
patent: 5358546 (1994-10-01), Rieke
Journal of The American Chemical Society, vol. 106, No. 11, 30 May 1984, DC US, pp. 3368-3370, XP002030288 E. Nakamura: "Copper-Catalyzed Acylation and Conjugate Addition of Zinc Homoenolate. Synthesis of 4- and 6-oxo esters."
Tetrahedron Letters, vol. 35, No. 39, 26 Sep. 1994, Oxford GB, pp. 7205-7208, XP00465075, M.V. Hanson, "Direct Formation of Secondary and Tertiary Alkylzinc Bromides".
J. Org. Chem. 1988, 53, 2390-2392.
The Direct Formation of Functionalized Alkyl (aryl) zinc Halides by Oxidative Addition of Highly Reactive Zinc with Organic Halides and Their Reactions with Acid Chlorides, .alpha.,.beta.-Unsaturated Ketones, and Allylic, Aryl, and Vinyl Halides, The Journal of Organic Chemistry, 1991, vol. 56, pp. 1445-1453.
1,4-Additions of the Highly Functionalized Copper Reagents RCu(CN)Znl . 2 BF.sub.3 to Trisubstituted Enones. A New BF.sub.3 Promoted Cyclization Reaction, Tetrahedron Letters, Yeh et al., vol. 29, No. 51, pp. 6693-6696, 1988.
2-Cyanoethylzinc Iodide: A New Reagent with Reactivity Umpolung, Tetrahedron Letters, Yeh and Knochel, vol. 29, No. 20, pp. 2395-2396, 1988.
Zhu et al., Tetrahedron Lett., vol. 32, p. 2865 (1991).
B.M. Trost and R. A. Kunz, J. Org. Chem. 39, 2648 (1974).

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