Herein we report a Ni-catalyzed reductive
transamidation of conveniently
available N-acyl benzotriazoles with alkyl, alkenyl,
and aryl nitro compounds, which afforded various amides with good
yields and a broad substrate scope. The same catalytic reaction conditions
were also applicable for N-sulfonyl benzotriazoles,
which could undergo smooth reductive coupling with nitroarenes and
nitroalkanes to afford the corresponding sulfonamides.
β‐Keto amides are a versatile class of compounds that find wide applications in organic chemistry owing to the juxtaposition of multiple reaction sites within their molecular structures. Due to the importance of β‐keto amides in modern organic chemistry, numerous novel preparation methods, synthetic applications and unprecedented reactivities have been recorded over the past decade. Taking advantage of transition‐metal‐catalysis and organocatalysis, β‐keto amides have emerged into a jack‐of‐all‐trades building block for many stereoselective or tandemized multicomponent reactions. But so far, no reviews have been documented on these recent achievements with β‐keto amides. Our Review aims to provide a thorough summary regarding: (a) the synthesis of β‐keto amides, (b) the reactivities of β‐keto amides, (c) the synthetic applications of β‐keto amides in various important heterocyclic compounds, and (d) the coordination of β‐keto amides with main group elements and transition metals and the relevant applications.
A facile synthesis of 4H-benzo [d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo [d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.
A well‐defined N‐heterocyclic carbene‐palladacycles (NHC‐Pdcycle) by introducing alkoxy group was synthesized, and its structure was confirmed using single‐crystal X‐ray diffraction. The complex as catalyst exhibited high catalytic activity in Buchwald‐Hartwig and Suzuki‐Miyaura coupling reactions involving (hetero)aryl chlorides. Remarkably, the protocol with a wide range of substrate compatibility is suitable for the gram‐scale synthesis of Piribedil, a clinical drug for the treatment of Parkinson's disease, highlighting its potential applications in pharmaceutical synthesis.
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