An organocatalyst bound α-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions.
@article{Motaleb2018AnOB,
title={An organocatalyst bound $\alpha$-aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions.},
author={Abdul Kadir Bin Motaleb and Asish Bera and Pradip Maity},
journal={Organic \& biomolecular chemistry},
year={2018},
volume={16 28},
pages={
5081-5085
}
}A catalyst bound α-aminoalkyl radical intermediate from iminium is developed to control its formation and reactivity with aerobic oxygen. The influence of the catalyst was demonstrated via the ease of radical intermediate formation and its subsequent reactivity, including the first catalyst-controlled enantioselective aerobic oxidation with a chiral phosphite catalyst.
13 Citations
Base-promoted aerobic oxidation of N-alkyl iminium salts derived from isoquinolines and related heterocycles
- Chemistry
- 2020
Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline,…
Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles
- Chemistry
- 2021
The selective C1–H/C4–H carbonylation of N-methyleneiminium salts catalyzed by visible-light photoredox reactions and oxygen in the air has been reported.
Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis.
- Chemistry, BiologyOrganic & biomolecular chemistry
- 2020
A visible-light-mediated process for dehydrogenation of amines has been described, showing a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification.
Phosphite Catalyzed C-H Allylation of Azaarenes via an Enantioselective [2,3]-Aza-Wittig Rearrangement.
- Chemistry, BiologyAngewandte Chemie
- 2019
This method provides efficient access to tertiary and quaternary chiral centers in isoquinoline, quinoline, and pyridine systems, tolerating a broad variety of substituents on both allyl part and azaarenes.
Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines†
- ChemistryChemical science
- 2021
This method provides efficient access to tertiary and quaternary stereogenic centers in pyridine systems, which are prevalent in drugs, bioactive natural products, chiral ligands, and catalysts, following the understanding of the stereoretentive process.
Electrochemical regioselective selenylation/oxidation of N-alkylisoquinolinium salts via double C(sp2)-H bond functionalization.
- Chemistry, BiologyChemical communications
- 2020
Antiviral bioassays demonstrated that compound 3j exhibited excellent antiviral activity against tobacco mosaic virus (TMV), and its inhibition rate was up to 90%.
A facile synthesis of 4-azaisoindoles and their transformation into novel pyrrole-fused 2-pyridones
- Chemistry
- 2020
Aerobic Oxidations in Asymmetric Synthesis: Catalytic Strategies and Recent Developments
- ChemistryFrontiers in Chemistry
- 2021
This review highlights recent achievements in catalytic enantioselective oxidations utilizing molecular oxygen as the sole oxidant, with focus on the mechanisms of dioxygen activation and chirogenesis in these transformations.
References
SHOWING 1-10 OF 35 REFERENCES
Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.
- ChemistryJournal of the American Chemical Society
- 2015
This method features a dual-catalyst protocol that combines transition metal photoredox catalysis with chiral Lewis acid catalysis and provides an effective, general strategy to generate and control the reactivity of photogenerated reactive intermediates.
Decarboxylative Arylation of α-Amino Acids via Photoredox Catalysis: A One-Step Conversion of Biomass to Drug Pharmacophore
- Chemistry, BiologyJournal of the American Chemical Society
- 2014
The direct decarboxylative arylation of α-amino acids has been achieved via visible light-mediated photoredox catalysis. This method offers rapid entry to prevalent benzylic amine architectures from…
Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines.
- ChemistryJournal of the American Chemical Society
- 2015
A redox neutral, highly enantioselective coupling between N-arylaminomethanes and N-sulfonyl aldimines was developed by harnessing the efficient catalysis of P-spiro chiral arylaminophosphonium…
Metallophosphites as umpolung catalysts: the enantioselective cross silyl benzoin reaction.
- ChemistryJournal of the American Chemical Society
- 2004
Carbonyl polarity reversal (umpolung) has been realized employing metallophosphites as catalysts, giving optically active silyl ether-protected benzoin adducts.
Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions.
- Chemistry, BiologyChemical communications
- 2016
This new umpolung synthesis of amines, which exploits the high nucleophilicity of a putative α-amino radical intermediate generated via single electron reduction of the in situ generated imine from the Hantzsch ester terminal reductant, is efficient, operationally simple, broad in scope and offers a complementary strategy to existing synthetic approaches.
Enantioselective organocatalytic alkylation of aldehydes and enals driven by the direct photoexcitation of enamines.
- ChemistryJournal of the American Chemical Society
- 2015
Mechanistic investigations reveal the previously hidden ability of transiently generated enamines to directly reach an electronically excited state upon light absorption while successively triggering the formation of reactive radical species from the organic halides.
Photoinduced set generation of α-amineradicals : A practical method for the synthesis of pyrrolidines and piperidines
- Chemistry
- 1989
Light-Mediated Reductive Debromination of Unactivated Alkyl and Aryl Bromides
- Chemistry
- 2016
Cleavage of carbon–halogen bonds via either single-electron reduction or atom transfer is a powerful transformation in the construction of complex molecules. In particular, mild, selective…
Sulfur-ylide-mediated synthesis of functionalized and trisubstituted epoxides with high enantioselectivity; application to the synthesis of CDP-840.
- ChemistryAngewandte Chemie
- 2003
A practical, catalytic, and asymmetric conversion of aldehydes into epoxides by using the sulfide 1 (Scheme 1) is reported, obtained in four steps in 48% overall yield from camphorsulfonyl chloride.
Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine.
- Chemistry, BiologyAngewandte Chemie
- 2015
A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2 CO3 under O2 and contrary to expectations, a 1:1 halogen-bonded complex forms.