The development of carbamoyl chlorides as synthons for various amide-containing molecules and heterocycles have been summarized and discussed in this review article. Carbamoyl chlorides can participate in a diverse range...
Transition metal-catalyzed carbonylation with carbon nucleophiles is one of the most prominent methods to construct ketones, which are highly versatile motifs prevalent in a variety of organic compounds. In comparison to the well-established palladium catalytic system, the nickel-catalyzed carbonylative coupling is much underdeveloped due to the strong binding affinity of CO to nickel. By leveraging easily accessible tert-butyl isocyanide as the CO surrogate, we present a nickel-catalyzed allylic carbonylative coupling with alkyl zinc reagent, allowing for the practical and straightforward preparation of synthetically important β,γunsaturated ketones in a linear-selective fashion with excellent trans-selectivity under mild conditions. Moreover, the undesired polycarbonylation process which is often encountered in palladium chemistry could be completely suppressed. This nickel-based method features excellent functional group tolerance, even including the active aryl iodide functionality to allow the orthogonal derivatization of β,γ-unsaturated ketones. Preliminary mechanistic studies suggest that the reaction proceeds via a π-allylnickel intermediate.
Herein, we disclose
a Ni-catalyzed formal aminocarbonylation of
primary and secondary unactivated aliphatic iodides with isocyanides
to afford alkyl amide, which proceeds via the selective monomigratory
insertion of isocyanides with alkyl iodides, subsequent β-hydride
elimination, and hydrolysis process. The reaction features wide functional
group tolerance under mild conditions. Additionally, the selective,
one-pot hydrolysis of reaction mixture under acid conditions allows
for expedient synthesis of the corresponding alkyl carboxylic acid.
Enantioenriched isoindolinone represents a valuable heterocycle motif, widely found in pharmaceuticals and biologically active nature products. We herein report a palladium-catalyzed asymmetric synthesis of 3,3-disubstituted isoindolinones via the tandem Heck/Suzuki...
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