Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization

Mirza, Yafia Kousin; Bera, Partha Sarathi; Mohite, Sachin Balaso; Pandey, Ajeet Kumar; Bera, Milan

doi:10.1039/d4qo00860j

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00860j

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Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization

Yafia Kousin Mirza,

Partha Sarathi Bera,

Sachin Balaso Mohite

et al.

Abstract: Silanes, a simple and common hydride source, are emphasized for their chemical stability, neat and easy-to-handle and usually not requiring any precautions upon activation by nickel catalysis. Their hydride donor...

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Cited by 3 publications

References 131 publications

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Ni‐Catalyzed Stereodivergent Synthesis of N‐Glycosides

Chen,

Martin

2024

Chemistry A European J

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Herein, we describe a stereoselective Ni‐catalyzed N‐glycosylation of glycals. The reaction is enabled by addition of an in situ generated nickel hydride across an olefin prior to C–N bond‐formation. Stereodivergence can be accomplished on kinetic or thermodynamic grounds, thus giving access to either α‐ or β‐N‐glycosides with equal ease. The protocol is distinguished by its operational simplicity, generality and exquisite selectivity, thus offering a new gateway to expedite the synthesis of N‐glycosides.

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Ni‐Catalyzed Stereodivergent Synthesis of N‐Glycosides

Chen,

Martin

2024

Chemistry A European J

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Nickel-Catalyzed Regio- and Stereoselective Hydroalkylation of Allenes: Exploiting the Unique Reactivity of Diazo Compounds as an Alkylating Source

Karmakar,

Bae,

Kim

et al. 2024

ACS Catal.

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The reactivity of allenes has historically been limited with no previous examples of their hydroalkylation using diazo compounds in any transition-metal catalytic framework. In this study, we present a Ni-catalyzed regio-and stereoselective hydroalkylation reaction of allenes utilizing diazo compounds as alkylating agents. The success of this method can be attributed to the use of a pyridine-based P,N ligand, which combines the advantages of both phosphine and nitrogen ligands. Additionally, the carbonyl group in the diazo compound facilitates the formation of stable intermediates. Our detailed mechanistic studies reveal that the reaction proceeds through an initial interaction with the diazo compound, followed by engagement with the allene.

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Recent Advances in Transition Metal-Catalyzed Ring-Opening Reaction of Aziridine

Bera,

Mirza,

Sachdeva

et al. 2024

Compounds

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The smallest strained, saturated N-heterocycles, such as aziridine, can be a valuable building block in synthetic organic chemistry. Ring-opening reactions with various nucleophiles could be the most important strategy to synthesize various value-added molecular entities. Therefore, regioselective ring-opening reactions of aziridines with various heteroatomic nucleophiles and carbon nucleophiles establish a useful synthetic methodology to synthesize biologically relevant β-functionalized alkylamines. The regio-selective ring-opening of aziridines is highly dependent on the substrate combination, and stereochemical control is challenging for Lewis acid-promoted reactions. Therefore, the development of a robust, catalytic ring-opening process that assists in the accurate prediction of regioselectivity and stereochemistry is highly desirable. Consequently, a large number of publications detailing distinct methods for aziridine ring-opening reactions can be found in the literature. In this review, we discuss several transition metal catalyzed cross-coupling reaction protocols for the ring opening of substituted aziridines with various carbon nucleophiles.

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Silanes as a versatile hydride source for Ni–H catalysis: a promising tool for π-hydro functionalization

Abstract: Silanes, a simple and common hydride source, are emphasized for their chemical stability, neat and easy-to-handle and usually not requiring any precautions upon activation by nickel catalysis. Their hydride donor...

Cited by 3 publications

References 131 publications

Ni‐Catalyzed Stereodivergent Synthesis of N‐Glycosides

Ni‐Catalyzed Stereodivergent Synthesis of N‐Glycosides

Nickel-Catalyzed Regio- and Stereoselective Hydroalkylation of Allenes: Exploiting the Unique Reactivity of Diazo Compounds as an Alkylating Source

Recent Advances in Transition Metal-Catalyzed Ring-Opening Reaction of Aziridine

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