Electrooxidative Pd-Catalyzed Remote Hydrofunctionalization of Alkenes with Nucleophiles DOI

Seungdae Park,

Baeho Yang,

Do‐Hyun Lee

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(21), С. 15858 - 15868

Опубликована: Окт. 11, 2024

The catalytic hydrofunctionalization of alkenes with nucleophiles via the generation carbocationic intermediates has been extensively studied as an efficient strategy for regioselective installation functional groups on alkene feedstocks. However, since established methods are confined to functionalization position where is originally located, it highly desirable develop a broadly applicable platform that offers alternative regioselectivity otherwise challenging achieve existing protocols. Herein, we report remote method enabled by electrooxidative palladium hydride catalysis. key success formation carbocation intermediate through mechanistic pathway, which involves chain-walking process followed anodic oxidation organopalladium species. This allows terminal and internal broad range oxygen, carbon, nitrogen, fluoride nucleophiles, including complex drug-like molecules.

Язык: Английский

Heteroleptic (NHC/MIC) Biscarbene Ag(I) and Au(I) Complexes: Synthesis, Characterization and Catalytic Applications DOI Open Access

Francisco J. Ruiz‐Mendoza,

Emmanuel Campos‐Dominguez,

M. Guadalupe Torres‐Salazar

и другие.

ChemPlusChem, Год журнала: 2025, Номер unknown

Опубликована: Янв. 29, 2025

A series of hetero-biscarbene silver(I) and gold(I) complexes the general formula [NHC-M-MIC]PF6 (NHC=imidazol-2-ylidene, MIC=1,2,3-triazol-5-ylidene) have been prepared via treatment NHC-M-Cl precursors in reaction with an situ generated mesoionic carbene (MIC). The new heteroleptic fully characterized including NMR spectroscopy, elemental analysis, melting points single crystal X-ray diffraction. derivatives were employed successfully solvent free KA2 (ketone-alkyne-amine) coupling for preparation a quaternary carbon-containing propargyl amines while, biscarbenes, demonstrated good performance A3 (aldehyde, amine, alkyne) benzylic oxidation processes under low catalyst loadings.

Язык: Английский

Процитировано

0

Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol DOI
Takahiro Kawajiri, Masahiro Hosoya,

Satoshi Goda

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 29, 2025

We report a novel electrochemical oxidation of benzyl alcohols. found that trifluoroethanol plays role as hydrogen atom transfer (HAT) mediator, enabling the electron-deficient substrates are difficult to directly oxidize on electrode surfaces. Density functional theory calculations, cyclic voltammetry measurements, and constant potential electrolysis studies supported proposed HAT mechanism. Moreover, obtained carbonyl compounds could be functionalized in an one-pot manner, further highlighting their synthetic utility.

Язык: Английский

Процитировано

0

Electrooxidative Pd-Catalyzed Remote Hydrofunctionalization of Alkenes with Nucleophiles DOI

Seungdae Park,

Baeho Yang,

Do‐Hyun Lee

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(21), С. 15858 - 15868

Опубликована: Окт. 11, 2024

The catalytic hydrofunctionalization of alkenes with nucleophiles via the generation carbocationic intermediates has been extensively studied as an efficient strategy for regioselective installation functional groups on alkene feedstocks. However, since established methods are confined to functionalization position where is originally located, it highly desirable develop a broadly applicable platform that offers alternative regioselectivity otherwise challenging achieve existing protocols. Herein, we report remote method enabled by electrooxidative palladium hydride catalysis. key success formation carbocation intermediate through mechanistic pathway, which involves chain-walking process followed anodic oxidation organopalladium species. This allows terminal and internal broad range oxygen, carbon, nitrogen, fluoride nucleophiles, including complex drug-like molecules.

Язык: Английский

Процитировано

0