Palladium-Catalyzed Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Organic Halides in Aqueous Media

Emilio Alacid and Carmen Nájera

*Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, 03080-Alicante, Spain, Email: cnajeraua.es

E. Alacid, C. Nájera, J. Org. Chem., 2009, 74, 2321-2327.

DOI: 10.1021/jo802356n

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Abstract

Alkenyltrifluoroborates can be cross-coupled with allyl and benzyl chlorides using KOH as base in acetone-water (3:2) at 50 °C and low catalyst loadings of a 4-hydroxyacetophenone oxime derived palladacycle giving the corresponding 1,4-dienes and allylarenes, respectively. The use of overheated water as solvent and K₂CO₃ as base allows a coupling of alkenyltrifluoroborates with aryl and heteroaryl bromides.

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General Reaction Conditions for the Palladium-Catalyzed Vinylation of Aryl Chlorides with Potassium Alkenyltrifluoroborates

E. Alacid, C. Nájera, J. Org. Chem., 2009, 74, 8191-8195.

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ey Words

Suzuki Coupling, 1,4-Dienes, Benzylation

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ID: J42-Y2009-0870