ArticleNature chemistry2025
Synthesis of tertiary alkyl amines via photoinduced copper-catalysed nucleophilic substitution.
Article in Nature chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Copper-catalysed site-selective arylation of pyrazoles.Nature chemistry · 2026Article
- Decarboxylative carbonyl alkylative amination: A general and practical strategy for aliphatic amine synthesis.Science advances · 2026Article
- Potassium Bisulfite's Role in Developing a Robust Platform for EnantioenrichedJournal of the American Chemical Society · 2026Article
- Harnessing COJournal of the American Chemical Society · 2026Article
- Bidentate mixed-ligand strategy in dinuclear gold photoredox catalysis.Nature communications · 2025Article
- Deoxygenative C(Journal of the American Chemical Society · 2025Article
- Overcoming limitations in Chan-Lam amination with alkylboronic esters via aminyl radical substitution.Nature communications · 2025Article
- Radical Strategy to the Boron-to-Copper Transmetalation Problem:Journal of the American Chemical Society · 2025Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
In view of the high propensity of tertiary alkyl amines to be bioactive, the development of new methods for their synthesis is an important challenge. Transition-metal catalysis has the potential to greatly expand the scope of nucleophilic substitution reactions of alkyl electrophiles; unfortunately, in the case of alkyl amines as nucleophiles, only one success has been described so far: the selective mono-alkylation of primary amines to form secondary amines. Here, using photoinduced copper catalysis, we report the synthesis of tertiary alkyl amines from secondary amines and unactivated alkyl electrophiles, two readily available coupling partners. Utilizing an array of tools, we have analysed the mechanism of this process; specifically, we have structurally characterized the three principal copper-based intermediates that are detected during catalysis and provided support for the key steps of the proposed catalytic cycle, including the coupling of a copper(II)-amine intermediate with an alkyl radical to form a C-N bond.
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Registered trials
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