ArticleJournal of the American Chemical Society2018
Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
What it found
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Who cites it
23 citing papers in PubMed, 120 citations in OpenAlex.
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- Photothermal Conversion Promotes Challenging SAngewandte Chemie (International ed. in English) · 2026Article
- Simple Cobalt Nanoparticle-Catalyzed Reductive Amination for Selective Synthesis of a Broad Range of Primary Amines.Molecules (Basel, Switzerland) · 2025Article
- Lewis Acid-Catalyzed Sulfur Fluoride Exchange.Organic letters · 2024Article
- Effect of 6,6'-Substituents on Bipyridine-Ligated Ni Catalysts for Cross-Electrophile Coupling.ACS catalysis · 2024Article
- Multicomponent Synthesis of α-Branched Amines via a Zinc-Mediated Carbonyl Alkylative Amination Reaction.Journal of the American Chemical Society · 2024Article
- Modular α-tertiary amino ester synthesis through cobalt-catalysed asymmetric aza-Barbier reaction.Nature chemistry · 2024Article
- Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines.Angewandte Chemie (International ed. in English) · 2022Article
- Leveraging Electron-Deficient Iminium Intermediates in a General Synthesis of Valuable Amines.Angewandte Chemie (International ed. in English) · 2022Article
- Nutzung von elektronenarmen Iminiumintermediaten zur Synthese von wertvollen Aminen.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Photo-Induced Ruthenium-Catalyzed C-H Benzylations and Allylations at Room Temperature.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Late-StageJournal of the American Chemical Society · 2021Article
- Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes.Chemical science · 2021Article
- Lewis acid mediated, mild C-H aminoalkylation of azolesChemical science · 2021Article
- Article
- Preparation of α-amino acidsChemical science · 2020Article
- Article
- α-Branched amines by catalytic 1,1-addition of C-H bonds and aminating agents to terminal alkenes.Nature catalysis · 2019Article
- Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.Organic letters · 2019Article
- Deaminative Reductive Arylation Enabled by Nickel/Photoredox Dual Catalysis.Organic letters · 2019Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.