Tandem Hydroformylation-Biginelli Reaction

Fuchs, Daniela; Nasr‐Esfahani, Mahboobeh; Diab, Lisa; Šmejkal, Tomáš; Breit, Bernhard

doi:10.1055/s-0033-1339298

Cited by 8 publications

(1 citation statement)

References 12 publications

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“…In addition, carbonylation of alkyl iodides with amides was successfully achieved by a manganese-catalyzed radical reaction . Our and other groups reported palladium- or rhodium-catalyzed hydroamidocarbonylation of olefins using amides as reaction partners (Scheme B). Furthermore, the palladium-catalyzed carbonylation of aldehydes using urea derivatives as less nucleophilic coupling reagents has been reported, which allows the preparation of multisubstituted hydantoins in good yields (Scheme C) …”

Section: Introductionmentioning

confidence: 96%

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Wang

Neumann

et al. 2023

ACS Catal.

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A general and broadly applicable cobalt-catalyzed multicomponent 1,2-perfluoroalkylation carbonylation of alkenes has been developed. This protocol allows the synthesis of β-perfluoroalkyl-substituted amides, esters, and related derivatives using olefins, carbon monoxide, commercially accessible perfluoroalkyl iodides, and a variety of nucleophiles including low nucleophilic amides and urea derivatives in a one-pot manner. As an example, readily available trifluoroiodomethane can be utilized forming pharmaceutically relevant β-trifluoromethylated amides. To showcase the application potential, the perfluoroalkylation carbonylation process was applied to selected current drugs and biologically active molecules. The methodology permits a straightforward increase of the molecular complexity of olefins toward functionalized perfluoroalkylated building blocks in a regioselective manner.

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Section: Introductionmentioning

confidence: 96%

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Wang

Neumann

et al. 2023

ACS Catal.

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1,3‐Dicarbonyls in Multicomponent Reactions

Bugaut¹,

Constantieux²,

Coquerel³

et al. 2014

Multicomponent Reactions in Organic Synthesis

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Rhodium‐Catalysed Tandem Hydroformylation/Arylation Reaction with Boronic Acids

et al. 2014

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A new efficient multicatalytic process involving a single catalyst to promote tandem hydroformylation/arylation reactions is disclosed. The effect of the rhodium ligand was evaluated and the rhodium/triphenylphosphine catalytic system was selected to apply the methodology to different olefins and boronic acids. High yields (up to 89%) and good to excellent isomer ratios (up to 98:2) were achieved using aryl olefins as starting materials. This new methodology allows the preparation of secondary alcohols, from simple olefins, and paves the way for the synthesis of high-value products, namely vinylindole and anethole derivatives. COMMUNICATIONSScheme 2. Transformation of olefins into secondary alcohols using Rh(I)/PPh 3 a multicatalytic tandem hydroformylation/arylation reaction.

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Tandem Hydroformylation-Biginelli Reaction

Abstract: The combination of a tandem process with a multicomponent reaction is a new approach to high atom-economic synthesis. A tandem hydroformylation-Biginelli reaction sequence has been developed leading to a variety of functionalized 4-alkyl-substituted 3,4-dihydropyrimidin-2(1H)-ones.

Cited by 8 publications

References 12 publications

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

1,3‐Dicarbonyls in Multicomponent Reactions

Rhodium‐Catalysed Tandem Hydroformylation/Arylation Reaction with Boronic Acids

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