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Publisher: Cambridge : RSC × Subject: Addition reactions × Subject: Amides ×

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    Pd/Cu-Catalyzed amide-enabled selectivity-reversed borocarbonylation of unactivated alkenes
    (Cambridge : RSC, 2021) Wu, Fu-Peng; Wu, Xiao-Feng
    The addition reaction between CuBpin and alkenes to give a terminal boron substituted intermediate is usually fast and facile. In this communication, a selectivity-reversed procedure has been designed and established. This selectivity-reversed borocarbonylation reaction is enabled by a cooperative action between palladium and copper catalysts and proceeds with complete regioselectivity. The key to the success of this transformation is the coordination of the amide group and slower CuBpin formation by using KHCO3as the base. A wide range of β-boryl ketones were produced from terminal unactivated aliphatic alkenes and aryl iodides. Further synthetic transformations of the obtained β-boryl ketones have been developed as well. © The Royal Society of Chemistry 2021.
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    Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst
    (Cambridge : RSC, 2019) Guo, Beibei; de Vries, Johannes G.; Otten, Edwin
    Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H2O to a wide variety of aliphatic and (hetero)aromatic nitriles in tBuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile. This journal is © The Royal Society of Chemistry.