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ChemInform Abstract: Palladium‐Catalyzed Reaction of Tributyltin Hydride. Regiospecifically Controlled Formation of α‐Bromo‐α,α‐Disubstituted Ketones from Tributyltin β‐Ketocarboxylates.

F. GUIBE, H. X. ZHANG, G.G.A. Balavoine

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Abstract

Abstract The α‐disubstituted allylic β‐keto esters (Ia) ‐ (Id), (Va), and (Vb) react with tributyltin hydride (II) in the presence of a palladium catalyst to give the corresponding tributylstannyl‐β‐ketocarboxylates which are converted to the highly substituted α‐bromoketones (IVa) ‐ (IVd), (VIa), and (VIb) by treatment with N‐bromosuccinimide (III) in situ.

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What this paper is about

Abstract The α‐disubstituted allylic β‐keto esters (Ia) ‐ (Id), (Va), and (Vb) react with tributyltin hydride (II) in the presence of a palladium catalyst to give the corresponding tributylstannyl‐β‐ketocarboxylates which are converted to the highly substituted α‐bromoketones (IVa) ‐ (IVd), (VIa), and (VIb) by treatment with N‐bromosuccinimide (III) in situ.

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Available abstract

Abstract The α‐disubstituted allylic β‐keto esters (Ia) ‐ (Id), (Va), and (Vb) react with tributyltin hydride (II) in the presence of a palladium catalyst to give the corresponding tributylstannyl‐β‐ketocarboxylates which are converted to the highly substituted α‐bromoketones (IVa) ‐ (IVd), (VIa), and (VIb) by treatment with N‐bromosuccinimide (III) in situ.

Key concepts: Tributyltin hydride, Chemistry, Tributyltin, Allylic rearrangement, Palladium, Catalysis, Medicinal chemistry, Hydride

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ChemInform Abstract: Palladium‐Catalyzed Reaction of Tributyltin Hydride. Regiospecifically Controlled Formation of α‐Bromo‐α,α‐Disubstituted Ketones from Tributyltin β‐Ketocarboxylates. — Research Paper | ScholarLens