Ex Situ Generation of D₂ for Reductive Deuteration: Scope and Application to Late-Stage Functionalization

The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1571 - 1584

Опубликована: Янв. 21, 2025

An efficient deuteration method through the ex situ generation of D2 for reductive biologically significant α-substituted acrylic acids and enamide derivatives is reported. This was successfully applied to synthesis deuterated analogs marketed NSAIDs such as ibuprofen, flurbiprofen, naproxen. Additionally, it facilitates late-stage enamides N-vinylated drugs. Moreover, extended N-viny azoles, cinnamic acid derivatives, other unsaturated substrates toward reaction. technique utilizes D2O a safe economical deuterium source. Notably, reaction performed in standard fume hood setup, ensuring ease handling enhanced practicality.

Язык: Английский

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Ex Situ Synthesis of N-Capped Peptides in the Solution Phase via Palladium-Catalyzed Aminocarbonylation Utilizing Chloroform-COware

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

We report the synthesis of N-capped peptides under mild conditions using oxidative aminocarbonylation aryl iodides and peptide esters as nucleophiles in solution phase. Ex situ chloroform chamber A generates CO, which diffuses to B, contains other reactants. This method offers at 80 °C for 12 h. synthesized 36 this method, including an anticancer drug bortezomib analogue, with isolated yield ranging from 52 91%. The present gives easy access previously inaccessible N-capping groups, heteroaromatic ring-capped enable robust analogue designs peptide-based discovery.

Язык: Английский

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Robust Noble Metal-Free Photoconversion of CO₂ to CO with a Molecule/MOF Hybrid Catalyst for Straightforward Two-Chamber Organic Carbonylation

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 3546 - 3557

Опубликована: Фев. 12, 2025

Язык: Английский

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Exploiting Chloroform-COware Chemistry for Pd-Catalyzed Carbonylation of Naturally Occurring and Medicinally Relevant Phenols

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(13), С. 9275 - 9286

Опубликована: Июнь 20, 2024

In this study, a ligand-free palladium-catalyzed carbonylation of phenols is conducted under ambient conditions, utilizing the "Chloroform-COware" chemistry. The developed methodology enables conversion diverse medicinally relevant phenols, encompassing both natural and synthetic derivatives, into their respective aryl ester counterparts. This transformation achieved through reaction with broad spectrum heteroaryl iodides. protocol characterized by its simplicity, generality, wide substrate scope, delivering bioactive derivatives in good to excellent yields. A direct comparison one-pot approach, resulting poor yields esters, highlights superior efficiency two-chamber setup (COware). Moreover, we successfully applied technique for gram-scale synthesis postmodification synthesized pharmaceutically important benzocoumarin core.

Язык: Английский

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Selective hydrogenation of unsaturated vinyl ethers in two‑chamber gauge‐reactor

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(7)

Опубликована: Май 11, 2024

Abstract A pressure gauge was incorporated into a two‐chamber glass H‐tube to continuously monitor the inside reactor when working with gases. The ex situ generated H 2 , D acetylene and CO were tested in reactors, calibration curves plotted. series of unsaturated compounds two or more double C=C bonds accessible for hydrogenation synthesized hydrogenation. proceeded well due constant control, desired products isolated good yields. same procedures then carried out using steel autoclaves verify results compare them. Surprisingly, almost obtained, confirming effectiveness self‐made reactors. mechanism further investigated D‐labeled reagents. kinetics studied both manometric reactors autoclaves, which showed similar nature main process reaction units. Thus, created can be effectively used barometric transformations instead appropriate cases.

Язык: Английский

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1-Iodoglycal: A Versatile Intermediate for the Synthesis of d-Glyco Amides and Esters Employing Carbonylative Cross-Coupling Reaction

ACS Omega, Год журнала: 2024, Номер 9(29), С. 31732 - 31744

Опубликована: Июль 11, 2024

In this study, we present the development of two catalytic processes: a Pd-PEPPSI-catalyzed aminocarbonylation and Pd(OAc)

Язык: Английский

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Iodoaniline Dependent Formation of N‐Aroylguanidines versus 2‐Aminoquinazolinones from Palladium(0) Catalysed Aminocarbonylation of N‐Arylguanidines

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 16, 2024

Abstract A family of N , N′ ‐diaryl‐ N′′ ‐(pyridine‐2‐ylmethyl)guanidines ( B ) were prepared in 70 %–92 % yields and subjected to palladium(0) catalyzed aminocarbonylation reactions with aryl iodides using CsOH/CHCl 3 mixture as CO surrogate afford the corresponding ‐aroylguanidines C %–93 yields. gram scale synthesis was reported for a representative example. When aforementioned reaction carried out 2‐iodoaniline an electrophile, either two distinct 2‐aminoquinazolinones D E or one these are formed. The scope guanidines explored both above‐mentioned reactions. role directing group substrates upon successful guanidines, is outlined. pair ‐aroylguanidines, PhI(OAc) 2 afforded 2‐aminobenzimidazoles, T unanticipated core. Plausible mechanisms formation

Язык: Английский

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The [PdCl2(Xantphos)] Complex Efficiently Catalyzed the Methoxycarbonylation of Iodobenzene to Methyl Benzoate

Catalysts, Год журнала: 2024, Номер 14(10), С. 660 - 660

Опубликована: Сен. 24, 2024

The [PdCl2(Xantphos)] complex, in comparison with several [PdCl2(P–P)] complexes having different diphosphine chelating ligands (P–P), is very active as a catalyst for the carbonylation of iodobenzene to methyl benzoate. run conditions and influence cocatalysts have been also studied further improve catalytic activity. optimization system allowed obtain TOFs ca. 260,000 h−1. addition some additives able reduce possible deactivation increase TOF 15%. best positive results were obtained by adding reducing agents such ferrocene, which leads higher than 300,000

Язык: Английский

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Carbonylative synthesis of 2-(trifluoromethyl)quinazolin-4(3H)-ones from trifluoroacetimidoyl chlorides and amines based on an activated carbon fibers supported palladium catalyst

New Journal of Chemistry, Год журнала: 2024, Номер 48(24), С. 10891 - 10896

Опубликована: Янв. 1, 2024

Activated carbon fibers, known for their unique physical and chemical properties, are increasingly utilized in diverse industries, including textiles fabrics, can serve as ideal supports of heterogeneous palladium catalysts.

Язык: Английский

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Pd-Catalyzed Hydrogenation of Unsaturated Terpenoids in Two-Chamber Reactors

Russian Journal of General Chemistry, Год журнала: 2024, Номер 94(4), С. 743 - 748

Опубликована: Апрель 1, 2024

Язык: Английский

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