Active Metals by Furstner A PDF

By Furstner A

ISBN-10: 3527273557

ISBN-13: 9783527273553

ISBN-10: 3527279385

ISBN-13: 9783527279388

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CuCN(LiBr)z CuSCN(LiBr)2 Cul-PRu3 CUI-PBu~ CUI-PBU~ CUT-PBu? Temp. 5 13 26 1 1 21 25 26 -SO -30 24 10 60 60 110 20 110 I05 75 1 20 60 150 15 20 65 130 170 5 30 5 5 10 100 80 50 35 0 0 0 78 9 I 13 0 99 86 56 31 8 28 2 3 5 24 22 27 3 42 31 6 0 31 28 28 50 0 25 3 60 76 71 70 61 x 0 3 5 5 2 0 0 0 0 0 sely, dropwise addition of the alkyl bromide to active copper at low temperature is not desirable and usually forms considerable amounts of homocoupled products. The active copper prepared utilizing triphenylphosphine gave less than 1% of homocoupled product with alkyl bromides.

Consequently, the active copper formed by this method was prone to sinter, giving larger particles upon extended stining or prolonged periods of standing. As a result, the reactivity of the copper metal was reduced. It was also found that substitution of the potassium metal by lithium resulted in much longer reduction times, giving a copper metal that was relatively unreactive. The reactivity of the copper metal was determined by measuring its ability to homocouple organic halides, analogous to the Ullman reaction.

Table 1- 16 shows examples of this type of transformation. The use of Rieke zinc allows a wide varety of functional groups to be included [58]. 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.

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Active Metals by Furstner A


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