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  • Title: Ni-catalyzed reductive coupling of alkyl acids with unactivated tertiary alkyl and glycosyl halides.
    Author: Zhao C, Jia X, Wang X, Gong H.
    Journal: J Am Chem Soc; 2014 Dec 17; 136(50):17645-51. PubMed ID: 25415424.
    Abstract:
    This work highlights Ni-catalyzed reductive coupling of alkyl acids with alkyl halides, particularly sterically hindered unactivated tertiary alkyl bromides for the production of all carbon quaternary ketones. The reductive strategy is applicable to α-selective synthesis of saturated, fully oxygenated C-acyl glycosides through easy manipulations of the readily available sugar bromides and alkyl acids, avoiding otherwise difficult multistep conversions. Initial mechanistic studies suggest that a radical chain mechanism (cycle B, Scheme 1) may be plausible, wherein MgCl2 promotes the reduction of Ni(II) complexes.
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