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Giovannini R, Stüdemann T, Devasagayaraj A, et al. New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers. J Org Chem. 1999;64(10):3544-3553doi: 10.1021/jo982317b.
Giovannini, R., Stüdemann, T., Devasagayaraj, A., Dussin, G., & Knochel, P. (1999). New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers. The Journal of organic chemistry, 64(10), 3544-3553. https://doi.org/10.1021/jo982317b
Giovannini, Riccardo, et al. "New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers." The Journal of organic chemistry vol. 64,10 (1999): 3544-3553. doi: https://doi.org/10.1021/jo982317b
Giovannini R, Stüdemann T, Devasagayaraj A, Dussin G, Knochel P. New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers. J Org Chem. 1999 May 14;64(10):3544-3553. doi: 10.1021/jo982317b. PMID: 11674479.
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J Org Chem. 1999 May 14;64(10):3544-3553. doi: 10.1021/jo982317b.

New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp(3) Centers.

The Journal of organic chemistry

Riccardo Giovannini, Thomas Stüdemann, Arokiasamy Devasagayaraj, Gaëlle Dussin, Paul Knochel

Affiliations

  1. Fachbereich Chemie der Philipps-Universität Marburg, Hans-Meerwein-Strasse, D-35043 Marburg, Germany, and Institut für Organische Chemie der Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, D-81377 München, Germany.

PMID: 11674479 DOI: 10.1021/jo982317b

Abstract

The presence of a remote unsaturation (double bond, carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)(2) (7.5-10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)(2) as a catalyst (7.5-10 mol %; -35 degrees C, 5-10 h) leading to a broad range of polyfunctional cross-coupling products.

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