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Negishi Cross-Coupling Reaction

Negishi cross-coupling reaction   Named Reactions in Organic Synthesis
Reaction category:
Transition metal-catalyzed couplings

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In 1972 after the discovery of Nickel catalysed cross-coupling of alkenyl and aryl halides with Grignard reagents (Kumada cross-coupling) improvements in functional group tolerance were sought. It was realised that the answer lay in organometallic substrates with less electropositive metals than lithium and magnesium. From first studies in 1976 extensive research by E. Negishi demonstrated that the best results in terms of reactivity, yield and stereoselectivity were obtained when organozincs are used in the presence of palladium catalysts. Since then the palladium or nickel catalysed cross-coupling of organozincs with aryl, alkenyl or alkynyl halides is known as the Negishi cross-coupling reaction.

The use of organozinc reagents allows for a much greater variety of functional groups to be present in both coupling partners than is possible with the Kumada cross-coupling.

Other advantages include high reactivity, high regio- and stereoselectivity, their range of applications, few side reactions and limited toxicity.

The total synthesis of Motuporin , a cyclic pentapeptide that is a potent protein phosphatase-1 inhibitor and cytotoxin, utilized the Negishi cross-coupling reaction.



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Electrophilic aromatic substitution

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Some relevant Alfa Aesar products for the Negishi cross-coupling reaction:
Zinc chloride, anhydrous, 98+%
Zinc chloride, 0.7M soln. in THF
Zinc chloride, 1.9M in 2-MeTHF
Diphenylzinc, 98+%
Triphenylphosphine, 99+%
Triphenylphosphine, flake, 99%
Phenylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles
2-Pyridylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles Cyclohexylzinc bromide, 0.5M in THF, packaged under Argon in resealable ChemSeal™ bottles
Tetrakis(triphenylphosphine)palladium(0), 99.8% (metals basis), Pd 9% min
Tris(dibenzylideneacetone)dipalladium(0), complex with chloroform, Pd 20.6%
Dichloro[1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II), Pd 16.3%
Dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II), Pd 13.5-15.5%

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