Pd/C-Catalyzed Transfer Reduction of Aryl Chlorides with Sodium Formate in Water

2004 ◽  
Vol 2004 (16) ◽  
pp. 3404-3407 ◽  
Author(s):  
Antonio Arcadi ◽  
Giorgio Cerichelli ◽  
Marco Chiarini ◽  
Raquel Vico ◽  
Daniel Zorzan
Keyword(s):  
Sodium Formate ◽  
Aryl Chlorides

scholarly journals Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yanjun Li ◽  
Ziqi Ye ◽  
Yu-Mei Lin ◽  
Yan Liu ◽  
Yumeng Zhang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Sodium Formate ◽  
Bioactive Molecules ◽  
Co Catalyst ◽  
Aryl Chlorides ◽  
Aryl Amine ◽  
Drug Molecules ◽  
Photocatalytic System ◽  
Site Selective ◽  
Environmentally Friendly Method

AbstractDevelopment of practical deuteration reactions is highly valuable for organic synthesis, analytic chemistry and pharmaceutic chemistry. Deuterodehalogenation of organic chlorides tends to be an attractive strategy but remains a challenging task. We here develop a photocatalytic system consisting of an aryl-amine photocatalyst and a disulfide co-catalyst in the presence of sodium formate as an electron and hydrogen donor. Accordingly, many aryl chlorides, alkyl chlorides, and other halides are converted to deuterated products at room temperature in air (>90 examples, up to 99% D-incorporation). The mechanistic studies reveal that the aryl amine serves as reducing photoredox catalyst to initiate cleavage of the C-Cl bond, at the same time as energy transfer catalyst to induce homolysis of the disulfide for consequent deuterium transfer process. This economic and environmentally-friendly method can be used for site-selective D-labeling of a number of bioactive molecules and direct H/D exchange of some drug molecules.

Dechlorination of Aryl Chlorides with Sodium Formate Using a Homogeneous Palladium Catalyst

2006 ◽  
Vol 25 (4) ◽  
pp. 1052-1054 ◽  
Author(s):  
Margaret E. Logan ◽  
Mark E. Oinen
Keyword(s):  
Palladium Catalyst ◽  
Sodium Formate ◽  
Aryl Chlorides

Pd/C-Catalyzed Transfer Reduction of Aryl Chlorides with Sodium Formate in Water.

ChemInform ◽  
2004 ◽  
Vol 35 (46) ◽  
Author(s):  
Antonio Arcadi ◽  
Giorgio Cerichelli ◽  
Marco Chiarini ◽  
Raquel Vico ◽  
Daniel Zorzan
Keyword(s):  
Sodium Formate ◽  
Aryl Chlorides

scholarly journals Non-Innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides

2021 ◽  
Author(s):  
Alyah Chmiel ◽  
Oliver P. Williams ◽  
Colleen Chernowsky ◽  
Charles Yeung ◽  
Zachary Wickens
Keyword(s):  
Radical Anion ◽  
Sodium Formate ◽  
Coupling Reactions ◽  
Aryl Radical ◽  
Aryl Chloride ◽  
Aryl Chlorides ◽  
Radical Coupling ◽  
Substrate Reduction ◽  
Photocatalytic System

We describe a photocatalytic system that elicits potent photoreductant activity from conventional photocatalysts by leveraging radical anion intermediates generated <i>in situ</i>. The combination of isophthalonitrile and sodium formate promotes diverse aryl radical coupling reactions from abundant but difficult to reduce aryl chloride substrates. Mechanistic studies reveal two parallel pathways for substrate reduction both enabled by a key terminal reductant byproduct, carbon dioxide radical anion.

scholarly journals Non-Innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides

2021 ◽  
Author(s):  
Alyah Chmiel ◽  
Oliver P. Williams ◽  
Colleen Chernowsky ◽  
Charles Yeung ◽  
Zachary Wickens
Keyword(s):  
Radical Anion ◽  
Sodium Formate ◽  
Coupling Reactions ◽  
Aryl Radical ◽  
Aryl Chloride ◽  
Aryl Chlorides ◽  
Radical Coupling ◽  
Substrate Reduction ◽  
Photocatalytic System

We describe a photocatalytic system that elicits potent photoreductant activity from conventional photocatalysts by leveraging radical anion intermediates generated <i>in situ</i>. The combination of isophthalonitrile and sodium formate promotes diverse aryl radical coupling reactions from abundant but difficult to reduce aryl chloride substrates. Mechanistic studies reveal two parallel pathways for substrate reduction both enabled by a key terminal reductant byproduct, carbon dioxide radical anion.

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

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