By A. Furstner
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Extra info for Active Metals [chemistry]
In turn, thcse stable alkylcopper reagents arc able to cross-couple with benzoyl chloride at -78 "C to generate ketone products in excellent isolated yields, as shown in Table 1-23. Significantly, this thienyl-bascd activc copper adds oxidatively to ally1 chlorides and acetates at -78 "C to allow the direct formation of allylic organocopper reagents, accompanied by less than 10% of the Wurtz-type homocoupling products. In turn, these allylic organocopper reagents are capable of undergoing cross-coupling reactions with elcctrophilcs such as benzoyl chloride and benzaldehyde to give thc corresponding ketone and alcohol products respectively in good isolated yields, as shown in Table 1-24.
The use of Rieke zinc allows a wide varety of functional groups to be included . This same catalyst can be used to make 2-halo-olefins incorporating a high degree of functionality by reacting with 2,3-dibromopropene 1591. Examples of this type of reaction are shown in Table 1-17. 6 Cross-Coupling of Vinyl and Aryl Organozinc Reagents Using a Palladium Catalyst The organozinc can be transmetallated to palladium and the resulting organopalladiuni can subsequently be reacted with vinyl or aryl halides giving the cross-coupled products.
Although triphenylphosphine alkylcopper reagents are less nucleophilic, they give higher yields in cross-coupling reactions with acid chlorides since none of the primary alkyl bromide is lost as the homocoupled product. In the aryl cases, the choice of the phosphine ligand is not crucial in cross-coupling reactions with acid chlorides because aryl halides do not homocouple to the same extent as alkyl halides. Trialkylphosphine-based copper has also been used to form ketone-functionalized, remote ester-functionalized, stable ortho-halophen)ilcopper reagents and in the cyclization of u,w-dihaloalkanes .
Active Metals [chemistry] by A. Furstner