Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis

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Abstract: A frustrated Lewis pair‐catalyzed hydroboration of aromatic and aliphatic nitriles was developed. The catalyst provides the primary amines in high yields of 77–99% with catalyst loading as low as 2 mol%. The reaction displays high functional group tolerance towards esters, amides, nitro groups and aliphatic halides. The addition of the diborylated amines to ethyl 3‐phenylpropiolate proceeds with Z‐selectivity with d.r. of>99:1 in 77–90% yield over two steps. The reaction mechanism was investigated by control and computational experiments.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis ; day:31 ; month:08 ; year:2022 ; extent:1
Advanced synthesis & catalysis ; (31.08.2022) (gesamt 1)

Creator: Sieland, Benedikt
Hoppe, Axel
Stepen, Arne J.
Paradies, Jan H. H.

DOI: 10.1002/adsc.202200525

URN: urn:nbn:de:101:1-2022090115145934203831

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:38 AM CEST

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Sieland, Benedikt
Hoppe, Axel
Stepen, Arne J.
Paradies, Jan H. H.

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Frustrated Lewis Pair‐Catalyzed Hydroboration of Nitriles: FLP Versus Borenium Catalysis

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Other Objects (12)

Frustrated Lewis Pair Catalyzed Reactions

Nickel‐Catalyzed Thiolation of Aryl Nitriles

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Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis

Exploring Supramolecular Frustrated Lewis Pairs

Bifunctional Fluorophosphonium Triflates as Intramolecular Frustrated Lewis Pairs: Reversible CO 2 Sequestration and Binding of Carbonyls, Nitriles and Acetylenes

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Nickel‐Catalyzed Thiolation of Aryl Nitriles

Ferrocene : a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry

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Exploring Supramolecular Frustrated Lewis Pairs

Bifunctional Fluorophosphonium Triflates as Intramolecular Frustrated Lewis Pairs: Reversible CO 2 Sequestration and Binding of Carbonyls, Nitriles and Acetylenes

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Synthesis of α-keto acids and nitriles by enzyme catalysis

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Nickel‐Catalyzed Thiolation of Aryl Nitriles

Ferrocene : a suitable framework for polymerization catalysis and frustrated Lewis pair chemistry

Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis

Exploring Supramolecular Frustrated Lewis Pairs

Bifunctional Fluorophosphonium Triflates as Intramolecular Frustrated Lewis Pairs: Reversible CO 2 Sequestration and Binding of Carbonyls, Nitriles and Acetylenes

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