Alkyl Negishi cross-coupling

Achonduh GT, Hadei N, Valente C et al (2010) On the role of additives in alkyl-alkyl Negishi cross-couplings. Chem Commun 46 4109-4111. doi 10.1039/c002759f... 

McCann LC, Hunter HN, Clybinne JAC, Organ MG (2012) Higher-order zincates as transmetalators in alkyl-alkyl Negishi cross-coupling. Angew Chem Int Ed 51 7024-7027. doi 10.1002/anie.201203547... 

Zhou, J. Fu, G. C. Palladium-catalyzed Negishi cross-coupling reactions of unactivated alkyl iodides, bromides, chlorides, and tosylates. I. Am. Chem. Soc. 2003, 125, 12527-12530. 

This method can be exploited as part of a one-pot hydroalkylation of an internal alkyne. Thus, titanium-catalyzed syn hydrozincation [24], followed by Negishi cross-coupling with an alkyl halide, stereospecifically generates a trisubstituted olefin (Eq. 8). 

Table 4 Negishi cross-coupling reactions of alkyl electrophiles and organozinc halides...

Organozinc compounds have been extremely useful reagents in the Negishi cross-coupling reactions with alkyl and aryl halides creating a new C—C bond (Scheme 13.28). The Negishi Ni, Pd, or Fe mediated cross-coupling reactions have proved to be powerful tools in vast areas of synthesis. 

Negishi cross-coupling reactions of primary and secondary alkyl bromides and iodides are achieved when Ni(COD) is employed as the catalyst in the presence of a diamine ligands such as bupybox [95],... 

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