New developments in palladium catalysed cross coupling: The coupling of alkyl iodides with alkyl Grignard reagents
β Scribed by Paul L Castle; David A Widdowson
- Book ID
- 104219464
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 189 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Sumnary -The species generated by the in situ reduction of l,l'-bis(di--phenylphosphino)ferrocenepalladium dichl3&?s an effective catalyst for the cross coupling of alkyl iodides with alkyl Grignard reagents. 4 9 Isolated yields of major products, relative yields determined by g.1.c. analysis, no olefins from B-elimination reactions were detectable. This arises by homo-coupling when Grignard reagent formation is incomplete. No detectable yield. Ambient temperature. Also detected: 4-bromoanisole (37%).
Refluxing THF solution.
Also detected: anisole (83x1, the product of proton quenching of unreacted Grignard reagent.
π SIMILAR VOLUMES
Chlorophenyl alkyl sulfides are mono-arylated and -alkylated selectively with Grignard reagents, in the presence of Ni(PPh3)2C12, to give aryl-and alkyl-phenyl alkyl sulfides.
Treatment of secondary or tertiary alkyl bromides with alkyl Grignard reagents in the presence of catalytic amounts of silver bromide and potassium fluoride in CH 2 Cl 2 afforded the corresponding cross-coupling products in reasonable yields. Moreover, silver showed catalytic activity for the cross-