Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant was written by Xu, Hailiang;Zhao, Chenglong;Qian, Qun;Deng, Wei;Gong, Hegui. And the article was included in Chemical Science in 2013.Recommanded Product: 4-methoxypicolinonitrile This article mentions the following:
(Pinacolato)diboron was used as the terminal reductant which allowed the efficient Ni-catalyzed coupling of unactivated secondary and primary alkyl halides, generating the C(sp3)-C(sp3) coupling products in good yields. The mild catalytic conditions displayed an excellent functional group tolerance and good chemoselectivities which required only 1.5 equivalent of primary bromides for the coupling with secondary bromides. Mechanistic studies suggest that an in-situ organoborane/Suzuki process was not likely and was proved that the base and ligand had more profound impact on selecting this reductive coupling pathway. The good chemoselectivity appears to be evoked by the formation of Ni-Bpin catalytic intermediates which demands matched sizes and reactivities of the alkyl halide coupling partners for optimal coupling efficiency. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 4-methoxypicolinonitrile).
4-methoxypicolinonitrile (cas: 36057-44-0) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 4-methoxypicolinonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts