Radical electrophilic aromatic substitution of electron-deficient aryl halides via aerobic ternary electron donor-acceptor photocatalysis DOI Creative Commons

Jiayi Gu,

Yingfen Meng,

Zhuo Cheng

и другие.

Cell Reports Physical Science, Год журнала: 2024, Номер 5(10), С. 102230 - 102230

Опубликована: Окт. 1, 2024

Highlights•Ternary EDA exciplex induced alkyl aryl ether synthesis•Aerobic photocatalytic system•Good functional group compatibility and late-stage functionalization•Scalable synthesis of fine chemicalsSummaryThe direct use molecular oxygen as a clean, abundant, readily available reactant is one the green, sustainable, yet challenging methodologies for C–O bond construction to access diverse oxygenated compounds. Herein, we report ternary electron donor-acceptor complex system that utilizes O2 construct multiple bonds successively in single-step operation, enabling facile assembly ethers. Mechanistic investigation shows halide/2-tert-butyl-1,1,3,3-tetramethylguanidine/tetrahydrofuran generated situ plays an essential role, affording radical anion species captured by electrophilic form Meisenheimer-type intermediate, subsequently participates Williamson etherification process give products with good selectivity compatibility. This protocol not only enables rapid ethers but also allows chemicals, such proparacaine, decylparaben, sildenafil subunits, starting from halogenated compounds.Graphical abstract

Язык: Английский

Radical electrophilic aromatic substitution of electron-deficient aryl halides via aerobic ternary electron donor-acceptor photocatalysis DOI Creative Commons

Jiayi Gu,

Yingfen Meng,

Zhuo Cheng

и другие.

Cell Reports Physical Science, Год журнала: 2024, Номер 5(10), С. 102230 - 102230

Опубликована: Окт. 1, 2024

Highlights•Ternary EDA exciplex induced alkyl aryl ether synthesis•Aerobic photocatalytic system•Good functional group compatibility and late-stage functionalization•Scalable synthesis of fine chemicalsSummaryThe direct use molecular oxygen as a clean, abundant, readily available reactant is one the green, sustainable, yet challenging methodologies for C–O bond construction to access diverse oxygenated compounds. Herein, we report ternary electron donor-acceptor complex system that utilizes O2 construct multiple bonds successively in single-step operation, enabling facile assembly ethers. Mechanistic investigation shows halide/2-tert-butyl-1,1,3,3-tetramethylguanidine/tetrahydrofuran generated situ plays an essential role, affording radical anion species captured by electrophilic form Meisenheimer-type intermediate, subsequently participates Williamson etherification process give products with good selectivity compatibility. This protocol not only enables rapid ethers but also allows chemicals, such proparacaine, decylparaben, sildenafil subunits, starting from halogenated compounds.Graphical abstract

Язык: Английский

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