Pyrene-Based Organic Photoredox Catalysts for Carbon–Carbon Bond-Forming Reactions: Reductive Coupling of Aromatic Carbonyl and Imine Compounds DOI
Shusuke Okamoto, Daisuke Nagai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7718 - 7722

Published: Sept. 5, 2024

Metal-free photoredox catalysts built upon a pyrene core were developed for carbon-carbon bond-forming reactions. Among these catalysts, derivative containing urea moiety effectively facilitated the reductive coupling of aromatic carbonyl and imine compounds under blue LED irradiation. This process provided corresponding vicinal diols diamines in good yields.

Language: Английский

Photodriven Sm(III)-to-Sm(II) Reduction for Catalytic Applications DOI Creative Commons
Christian M. Johansen, Emily A. Boyd,

Drew E. Tarnopol

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(37), P. 25456 - 25461

Published: Sept. 3, 2024

The selectivity of SmI

Language: Английский

Citations

4
Chemo-Selective Electrochemical Pinacol Coupling of Aldehydes and Ketones Using TMSN3 as a Promoter DOI

Shengmei Guo,

Yunxiang Jiang,

Junpeng Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

The pinacol coupling is a significant method for carbon–carbon bond formation. Here, we present an efficient electrochemical approach of aldehydes and ketones using TMSN3 as sacrificial reagent. This exhibits broad applicability to aryl, heteroaryl, alkyl aldehydes/ketones with excellent chemo-selectivity high yields (40 examples, up 99% yield) under mild conditions. can also be applied in the selective reduction phthalimides hydroxyl lactams good yields. proposed mechanism was elucidated by control experiments cyclic voltammetry.

Language: Английский

Citations

0
Manganese-Promoted Electrochemical Imino-Pinacol Coupling to Access Vicinal Diamines DOI

Weihao Cui,

Xiaolong Xu, Cong Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 5, 2025

We herein introduce an electrochemical imino-pinacol coupling reaction to access the vicinal diamine scaffold. This green and convenient protocol employs in situ-generated imines as starting materials deliver a broad range of products under electroreductive conditions. Moreover, this is also applicable pinacol coupling. Mechanistic investigation suggests that Mn(III) additive essential for promoting SET reduction imine material preventing formation over-reduced amine side product.

Language: Английский

Citations

0
Successors of SmI2: Next Generation Metal, Photo and Electro‐Catalysis for Reductive Organic Synthesis DOI
Samarpita Senapati,

Subhendu Jena,

Manwar Box

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

Abstract Electron transfer plays a pivotal role in generating radical intermediates which are pillars of constructing complex molecular structure. Since the introduction by Kagan, SmI 2 played key single electron mediated reductive transformations. Despite significant applications high profile synthesis natural products, usage was discoursed due to weight reagent, less solubility and most importantly stoichiometric nature reactions. Recent years have witnessed renaissance photo‐and electro‐catalytic reactions more sustainable nature. A handful these showed potential replace as greener alternative. This prospective article aims demonstrate reducing systems use .

Language: Английский

Citations

0
Photoinduced pinacol coupling of carbon-carbon bonds via triethoxysilane or Hantzsch Ester DOI
Jianhua Liu,

Gelan Wang,

Chen Chen

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 579, P. 115088 - 115088

Published: April 5, 2025

Language: Английский

Citations

0
Divalent Intermediates in Lanthanide-Based Photocatalysts: Spectroscopic Characterization and Reactivity DOI Creative Commons
Monika Tomar, Anders Thapper, Andreas Orthaber

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 64(1), P. 594 - 605

Published: Dec. 23, 2024

The reduction of stable trivalent lanthanide species (Ln(III)) by the excited states organic chromophores is basis photocatalytic divalent lanthanide-mediated reactions. While indirect evidence photochemical formation reactive Ln(II) abundant, direct spectroscopic their presence scarce. Here, nine with absorptions covering near UV and visible ranges were systematically investigated in Ln(III) ions to evaluate ability reduce Eu(III) upon excitation light catalytically active Eu(II) species. Irradiated mixtures characterized using UV–vis absorption emission EPR spectroscopy. Several chromophore-Eu(III) combinations competent photocatalysts N,N-diisopropylethylamine or Zn terminal reductants. These results demonstrate that a variety visible-absorbing can efficiently generate from catalyze Ln(II)-mediated

Language: Английский

Citations

1
Dehydrogenative α,γ-Diphosphinylation of Allylamines Enabled by Photoinduced Cobaloxime Catalysis DOI
Jun Guo, Yana Zhang, Miaomiao Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 18, 2024

A regioselective radical α,γ-diphosphinylation of allylamines with secondary phosphine oxides by photoinduced cobaloxime catalysis is described. The reaction tolerates a wide range and oxides, affording α-amino diphosphine dioxides in moderate to good yields hydrogen evolution. synthesis new monoxide ligands the promising antitumor activities products demonstrate great potential applications this approach drug discovery. detailed mechanism studies indicate that likely proceeds through dehydrogenative allylic phosphinylation nucleophilic addition process.

Language: Английский

Citations

1
Photocatalyst for Visible-Light-Driven Sm(II)-Mediated Reductions DOI Creative Commons
Monika Tomar,

Caroline Bosch,

Jules Everaert

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

Commercially available coumarin 343 in combination with reducible Sm(III) ions catalyzed divalent lanthanide-mediated C═O, C-halogen, P-Cl, and N═N reductions at ambient temperature aqueous solvent mixtures. The catalyst absorbs visible light efficiently. active species is formed by photoinduced electron transfer from to the stable trivalent precursor, could be regenerated strictly 1 equiv of ascorbic acid.

Language: Английский

Citations

1
Pyrene-Based Organic Photoredox Catalysts for Carbon–Carbon Bond-Forming Reactions: Reductive Coupling of Aromatic Carbonyl and Imine Compounds DOI
Shusuke Okamoto, Daisuke Nagai

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7718 - 7722

Published: Sept. 5, 2024

Metal-free photoredox catalysts built upon a pyrene core were developed for carbon-carbon bond-forming reactions. Among these catalysts, derivative containing urea moiety effectively facilitated the reductive coupling of aromatic carbonyl and imine compounds under blue LED irradiation. This process provided corresponding vicinal diols diamines in good yields.

Language: Английский

Citations

0