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- Q902756 subject Q7458901.
- Q902756 subject Q8343673.
- Q902756 subject Q8408894.
- Q902756 abstract "The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (c-c) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used: The leaving group X is usually chloride, bromide, or iodide, but triflate and acetyloxy groups are feasible as well. X = Cl usually leads to slow reactions. The organic residue R = alkenyl, aryl, allyl, alkynyl or propargyl. The halide X' in the organozinc compound can be chloride, bromine or iodine and the organic residue R1 is alkenyl, aryl, allyl, alkyl benzyl, homoallyl, and homopropargyl. The metal M in the catalyst is nickel or palladium The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP or chiraphosPalladium catalysts in general have higher chemical yields and higher functional group tolerance.The Negishi coupling finds common use in the field of total synthesis as a method for selectively forming c-c bonds between complex synthetic intermediates. The reaction allows for the coupling of sp3, sp2, and sp carbons, (see orbital hybridization) which make it somewhat unique among the Palladium-catalyzed coupling reactions. Organozincs are moisture and air sensitive, so the Negishi coupling must be performed in an oxygen and water free environment, a fact that has hindered its use relative to other cross-coupling reactions that require less robust conditions (i.e. Suzuki reaction). However, organozincs are more reactive than both organostannanes and organoborates which correlates to faster reaction times.The reaction is named after Ei-ichi Negishi who was a co-recipient of the 2010 Nobel Prize in Chemistry for the discovery and development of this reaction.".
- Q902756 thumbnail NegishiScheme1.png?width=300.
- Q902756 wikiPageExternalLink negishi-coupling.shtm.
- Q902756 wikiPageExternalLink negishi-coupling.
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- Q902756 comment "The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (c-c) in the process. A palladium (0) species is generally utilized as the metal catalyst, though nickel is sometimes used: The leaving group X is usually chloride, bromide, or iodide, but triflate and acetyloxy groups are feasible as well. X = Cl usually leads to slow reactions.".
- Q902756 label "Negishi coupling".
- Q902756 depiction NegishiScheme1.png.