Negishi coupling reaction

Heck, Suzuki, Stille, and Negishi coupling reactions... 

Unlike normal all-carbon aryl halides, regioselective Negishi coupling reaction of 2,3-dibromofuran 27 with 2-furylzinc chloride was achieved at C(2) to afford bisfuran 28 [35]. 

G. Dutheuil, C. Paturel, X. Lei, S. Couve-Bonnaire, X. Pannecoucke, First stereospecific synthesis of ( )- or (Z)-a-fluoroenones via a kinetically controlled negishi coupling reaction, J. Org. Chem. 71 (2006) 4316-4319. 

Transition Metal Catalysis in tonic Liquids 241 5.2.4.4 Heck, Suzuki, Stille, and Negishi coupling reactions... 

Fig. 1 Nickel-catalyzed Negishi coupling reactions of alkyl halides 1 with organozinc reagents 2...

Peyrat, J.-F., Thomas, E., L Hermite, N., Alami, M., Brian, J.-D. Versatile palladium(ll)-catalyzed Negishi coupling reactions with functionalized conjugated alkenyl chlorides. Tetrahedron Lett. 2003,44, 6703-6707. 

Pannecoucke and co-workers developed a highly stereospecific synthesis of (Z)- and (E )-a-fluoroenones 66 through a kinetically controlled Negishi coupling reaction catalyzed by palladium (see Scheme 10.23) [32]. 

In efforts to prepare substituted methylthio-2V-heterocycles, researchers at Dupont discovered a new type of Negishi coupling reaction in which benzylic zinc reagents were found to undergo a Pd-catalyzed cross-coupling reaction at the C—S site. 2-(Methylthio) pyrimidine 50 was found to be a particularly reactive substrate for this reaction. Indeed, a 71% isolated yield using 1 mol% Pd( PPh J was obtained with benzyl zinc bromide and 2-(methylthio)pyrimidine in THF. This new cross-coupling method provides a convenient alternative to the use of pyrimidine halides [24]. 

Teraryls are readily synthesized from l,4-his(iodozincio)benzene by consecutive Negishi coupling reactions. Such is feasible because of the different reactivity of the two types of arylzinc reagents, products of the first coupling are less reactive toward the Pd catalyst. ... 

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