Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N -Alkoxyphthalimides

Pau Sarró; Albert Gallego-Gamo; Elies Molins; Roser Pleixats i Rovira; Carolina Gimbert Suriñach; Adelina Vallribera Massó; Albert Granados Toda

doi:10.1021/acs.orglett.5c03734

Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N -Alkoxyphthalimides

Pau Sarró, Albert Gallego-Gamo, Elies Molins, Roser Pleixats i Rovira, Carolina Gimbert Suriñach, Adelina Vallribera Massó, Albert Granados Toda

Institut de Ciència de Materials de Barcelona

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3 Cites (Scopus)

Resum

The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for β-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N -alkoxyphthalimides through hydrogen-bonded aggregates with ROH···F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studiesincluding UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenchingreveal a radical/polar crossover pathway.

Idioma original	Anglès
Pàgines (de-a)	11372-11377
Nombre de pàgines	6
Revista	Organic Letters
Volum	27
Número	40
DOIs	https://doi.org/10.1021/acs.orglett.5c03734
Estat de la publicació	Publicada - 10 d’oct. 2025

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10.1021/acs.orglett.5c03734

https://ddd.uab.cat/record/321532

MOLECULAS Y MATERIALES ORGANICOS PARA REACCIONES CATALITICAS ACTIVADAS MEDIANTE LA LUZ SOLAR
Gimbert Suriñach, C. (Investigador/a principal), Gallego Gamo, A. (Col.laborador/a) & Sarró Grane, P. (Col.laborador/a)
Fons Europeu de Desenvolupament Regional (FEDER)
1/09/22 → 31/08/25
Projecte: Projectes i Ajuts a la Recerca

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title = "Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N -Alkoxyphthalimides",

abstract = "The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for beta-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH center dot center dot center dot F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies-including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching-reveal a radical/polar crossover pathway.",

author = "Pau Sarr{\'o} and Albert Gallego-Gamo and Elies Molins and \{Pleixats i Rovira\}, Roser and \{Gimbert Suri{\~n}ach\}, Carolina and \{Vallribera Mass{\'o}\}, Adelina and \{Granados Toda\}, Albert",

note = "Publisher Copyright: {\textcopyright} 2025 The Authors. Published by American Chemical Society",

year = "2025",

month = oct,

day = "10",

doi = "10.1021/acs.orglett.5c03734",

language = "English",

volume = "27",

pages = "11372--11377",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "40",

}

TY - JOUR

T1 - Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N -Alkoxyphthalimides

AU - Sarró, Pau

AU - Gallego-Gamo, Albert

AU - Molins, Elies

AU - Pleixats i Rovira, Roser

AU - Gimbert Suriñach, Carolina

AU - Vallribera Massó, Adelina

AU - Granados Toda, Albert

PY - 2025/10/10

Y1 - 2025/10/10

N2 - The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for beta-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH center dot center dot center dot F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies-including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching-reveal a radical/polar crossover pathway.

AB - The generation and controlled reactivity of alkoxyl radicals remain challenging due to their high energy and tendency for beta-scission or hydrogen atom transfer events. Herein, we report a photoredox-catalyzed dioxygenation of alkenes enabled by the activation of fluorinated N-alkoxyphthalimides through hydrogen-bonded aggregates with ROH center dot center dot center dot F. This transformation proceeds under mild, metal-free conditions using an organophotocatalyst and a simple alcohol, affording a diverse range of dialkoxylated products with high functional group tolerance and good scalability. Mechanistic studies-including UV-Vis spectroscopy, NMR, cyclic voltammetry, and Stern-Volmer quenching-reveal a radical/polar crossover pathway.

U2 - 10.1021/acs.orglett.5c03734

DO - 10.1021/acs.orglett.5c03734

M3 - Article

C2 - 41026519

SN - 1523-7060

VL - 27

SP - 11372

EP - 11377

JO - Organic Letters

JF - Organic Letters

IS - 40

ER -

Organophotoredox Dioxygenation of Alkenes via ROH···F-Activated N -Alkoxyphthalimides

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MOLECULAS Y MATERIALES ORGANICOS PARA REACCIONES CATALITICAS ACTIVADAS MEDIANTE LA LUZ SOLAR

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