Carbonylative transformation of aryl halides and strong bonds via cheap metal catalysts and sustainable technologies

Green Synthesis and Catalysis, Год журнала: 2024, Номер 5(4), С. 211 - 269

Опубликована: Май 6, 2024

The development of catalytic carbonylation reactions has increased considerably. Although many reviews/chapters/books on have been published, summaries cheap metal-catalyzed aryl halides and other chemical bonds with high dissociation energy C-Y (Y = O, N, H) are still very rare. Focusing green sustainable chemistry, this review summarizes discusses the achievements carbonylative transformations (C(sp2)-X) strong based non-expensive metal catalysts (Co, Mn, Mo, Ni, Fe, Cu), photochemical electrochemical systems developed in recent decades.

Язык: Английский

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Visible light mediated iron-catalyzed addition of oxamic acids to imines

RSC Advances, Год журнала: 2024, Номер 14(18), С. 12528 - 12532

Опубликована: Янв. 1, 2024

Oxamic acids where shown to add imines, providing a broad range of α-aminoacid amides in generally good yields.

Язык: Английский

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Site-Selective Pyridine Carbamoylation Enabled by Consecutive Photoinduced Electron Transfer

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 15521 - 15527

Опубликована: Окт. 4, 2024

Язык: Английский

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Direct construction of aryl amide N-glycosides from glycosyl oxamic acids via photoredox palladium-catalyzed aminocarbonylations

Chem Catalysis, Год журнала: 2024, Номер unknown, С. 101109 - 101109

Опубликована: Сен. 1, 2024

Язык: Английский

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Silver‐Catalyzed Decarboxylative Coupling of Oxamic Acids with Styrenes to Synthesize E‐Cinnamamides: A Distinguish Reaction Pathway

ChemistryOpen, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

Abstract A silver‐catalyzed decarboxylative coupling of oxamic acids with styrenes has been developed to produce E ‐cinnamamides. Oxamic act as efficient precursors for carbamoy radicals. Based on the mechanistic experiments and intermediate analysis, proposed mechanism involves radical addition styrenes, followed by oxidation solvent participation, ultimately leading formation cinnamamides which is different from reported cases.

Язык: Английский

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Direct Photocatalytic Reductive Amidation of Nitroarenes: A Tandem Reduction–Decarboxylation Approach to Amide Bond Construction

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 15, 2025

We report a photocatalytic strategy for direct amide synthesis from readily available nitroarenes and benzoylformic acids using flavin as an efficient photocatalyst. This one-pot transformation proceeds through tandem reduction-decarboxylation-amidation sequence under mild blue light irradiation. Preliminary mechanistic studies indicated that nitrosoarene N-hydroxyamides could be the key intermediates. The method demonstrates broad substrate scope, excellent functional group tolerance, remarkable operational simplicity, it can conducted ambient atmosphere. Notably, this protocol represents significant advancement in step economy by directly employing diverse nitrogen sources, avoiding need pre-reduced amine

Язык: Английский

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Copper‐mediated Synthesis of N‐Aryl‐oxamic Acids.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(57)

Опубликована: Июль 25, 2024

Abstract The Cu‐catalyzed Ullmann‐Goldberg cross‐coupling between aryl iodides and oxamates is shown to afford the corresponding N ‐aryloxamates with yields ranging from moderate excellent, when oxamate precursor incorporates a bulky tertiary alkyl group effectively preventing product degradation under strongly basic reaction conditions. final oxamic acids are then generated through acid hydrolysis of in high yields. These were converted into urethanes using PIDA thermal conditions or visible‐light Fe‐LMCT process. While electron‐deficient ‐aryl provide efficiencies, electron‐rich counterparts led diminished due over‐oxidation induced by PIDA.

Язык: Английский

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Synthesis of succinyldiamides containing all-quaternary carbon center by photo-induced amidation/smiles rearrangement of alkenes

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

A novel, mild, and environmentally friendly method was developed for the synthesis of quaternary-carbon-containing succinyldiamides. This found to be compatible with many substrates.

Язык: Английский

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Redox-Neutral Decarboxylative Cross-Coupling of Oxamates with Aryl Bromides

ACS Organic & Inorganic Au, Год журнала: 2023, Номер 4(2), С. 223 - 228

Опубликована: Ноя. 29, 2023

Dual nickel-photoredox-enabled direct synthesis of amides through cross-coupling cesium oxamates with aryl bromides has been developed. This methodology's key advantages are mild reaction conditions, utilizing organic dye as a photocatalyst, employing readily available starting chemicals coupling partners, and late-stage carbamoylation pharmaceutically relevant molecules. DFT studies suggested that the nickel catalytic cycle proceeds via radical addition pathway prior to oxidative insertion.

Язык: Английский

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Cr-mediated photocatalytic decarboxylative coupling of alpha-oxo acids with benzylic pyridinium salts

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3242 - 3249

Опубликована: Янв. 1, 2024

We developed a method for chromium/photoredox dual catalytic synthesis of ketones using α-oxo acids with benzylic pyridinium salts.

Язык: Английский

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