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  • Title: Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes.
    Author: Cruz CL, Montgomery J.
    Journal: Chem Sci; 2021 Sep 22; 12(36):11995-12000. PubMed ID: 34667565.
    Abstract:
    A mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides has been developed. The catalytic system features the use of a common Ni(ii) precatalyst and a readily available bioxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The use of 1,5-hexadiene as an additive is an important reaction parameter that provides significant benefits in yield optimizations. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species that undergoes formal oxidative addition to the alkyl bromide via a reductive cross-coupling pathway.
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