ArticleThe Journal of organic chemistry2024
Reductive Amination of Carbonyl C-C Bonds Enables Formal Nitrogen Insertion.
Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
4 citing papers in PubMed.
- Formal nitrogen-to-carbon replacement in isoindolines to form indenesChemical science · 2026Article
- Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025Article
- Two-Step Constitutional Isomerization of Saturated Cyclic Amines Using Borane Catalysis.JACS Au · 2025Article
- Reductive Amination of Carbonyl C-C Bonds Enables Formal Nitrogen Insertion.The Journal of organic chemistry · 2024Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Given its relevance across numerous fields, reductive amination is one of the oldest and most widely used methods for amine synthesis. As a cornerstone of synthetic chemistry, it has largely remained unchanged since its discovery over a century ago. Herein, we report the mechanistically driven development of a complementary reaction, which reductively aminates the C-C σ-bond of carbonyls, not the carbonyl C-O π-bond, generating value-added linear and cyclic 3° amines in a modular fashion. Critical to our success were mechanistic insights that enabled us to modulate the resting state of a borane catalyst, minimize deleterious disproportionation of a hydroxylamine nitrogen source, and control the migratory selectivity of a key nitrenoid reactive intermediate. Experiments support the reaction occurring through a reductive amination/reductive Stieglitz cascade, via a ketonitrone, which can be interrupted under catalyst control to generate valuable
Identifiers
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Registered trials
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