Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles

Albert Gallego Gamo; Yingmin Ji; Tapas Maity; Remy Lalisse; Elies Molins; Roser Pleixats i Rovira; Carolina Gimbert Suriñach; Adelina Vallribera Massó; Osvaldo Gutierrez; Albert Granados Toda

doi:10.1021/acs.orglett.5c04624

Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles

Albert Gallego Gamo, Yingmin Ji, Tapas Maity, Remy Lalisse, Elies Molins, Roser Pleixats i Rovira, Carolina Gimbert Suriñach, Adelina Vallribera Massó, Osvaldo Gutierrez, Albert Granados Toda

Institut de Ciència de Materials de Barcelona

Producció científica: Contribució a revista › Article › Recerca › Avaluat per experts

1 Citació (Scopus)

Resum

We describe a transition-metal-free photocatalytic synthesis of CF-BCP-oxindoles via radical cascade annulation. This mild and sustainable protocol employs a bench-stable thianthrenium CF-BCP reagent and activated anilides under visible-light irradiation to efficiently assemble complex scaffolds bearing dual (CF and BCP) bioisosteric features. Mechanistic studies reveal that CF-BCP radical generation proceeds through a previously unreported electron donor-acceptor (EDA) complex between 4CzIPN and the thianthrenium salt, initiating a radical chain process. This method provides a practical photochemical platform for the late-stage incorporation of CF-BCP motifs into oxindole frameworks and expands the accessible bioisosteric chemical space for drug discovery.

Idioma original	Anglès
Pàgines (de-a)	248-253
Nombre de pàgines	6
Revista	Organic Letters
Volum	28
Número	1
DOIs	https://doi.org/10.1021/acs.orglett.5c04624
Estat de la publicació	Publicada - 23 de des. 2025

Accés al document

10.1021/acs.orglett.5c04624

https://ddd.uab.cat/record/324774

Com citar-ho

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title = "Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles",

abstract = "We describe a transition-metal-free photocatalytic synthesis of CF 3–BCP–oxindoles via radical cascade annulation. This mild and sustainable protocol employs a bench-stable thianthrenium CF 3–BCP reagent and activated anilides under visible-light irradiation to efficiently assemble complex scaffolds bearing dual (CF 3 and BCP) bioisosteric features. Mechanistic studies reveal that CF 3–BCP radical generation proceeds through a previously unreported electron donor–acceptor (EDA) complex between 4CzIPN and the thianthrenium salt, initiating a radical chain process. This method provides a practical photochemical platform for the late-stage incorporation of CF 3–BCP motifs into oxindole frameworks and expands the accessible bioisosteric chemical space for drug discovery.",

author = "\{Gallego Gamo\}, Albert and Yingmin Ji and Tapas Maity and Remy Lalisse and Elies Molins and \{Pleixats i Rovira\}, Roser and \{Gimbert Suri{\~n}ach\}, Carolina and \{Vallribera Mass{\'o}\}, Adelina and Osvaldo Gutierrez and \{Granados Toda\}, Albert",

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

year = "2025",

month = dec,

day = "23",

doi = "10.1021/acs.orglett.5c04624",

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TY - JOUR

T1 - Photochemical Construction of Trifluoromethyl Bicyclo[1.1.1]pentyl-heterocycles

AU - Gallego Gamo, Albert

AU - Ji, Yingmin

AU - Maity, Tapas

AU - Lalisse, Remy

AU - Molins, Elies

AU - Pleixats i Rovira, Roser

AU - Gimbert Suriñach, Carolina

AU - Vallribera Massó, Adelina

AU - Gutierrez, Osvaldo

AU - Granados Toda, Albert

PY - 2025/12/23

Y1 - 2025/12/23

N2 - We describe a transition-metal-free photocatalytic synthesis of CF 3–BCP–oxindoles via radical cascade annulation. This mild and sustainable protocol employs a bench-stable thianthrenium CF 3–BCP reagent and activated anilides under visible-light irradiation to efficiently assemble complex scaffolds bearing dual (CF 3 and BCP) bioisosteric features. Mechanistic studies reveal that CF 3–BCP radical generation proceeds through a previously unreported electron donor–acceptor (EDA) complex between 4CzIPN and the thianthrenium salt, initiating a radical chain process. This method provides a practical photochemical platform for the late-stage incorporation of CF 3–BCP motifs into oxindole frameworks and expands the accessible bioisosteric chemical space for drug discovery.

AB - We describe a transition-metal-free photocatalytic synthesis of CF 3–BCP–oxindoles via radical cascade annulation. This mild and sustainable protocol employs a bench-stable thianthrenium CF 3–BCP reagent and activated anilides under visible-light irradiation to efficiently assemble complex scaffolds bearing dual (CF 3 and BCP) bioisosteric features. Mechanistic studies reveal that CF 3–BCP radical generation proceeds through a previously unreported electron donor–acceptor (EDA) complex between 4CzIPN and the thianthrenium salt, initiating a radical chain process. This method provides a practical photochemical platform for the late-stage incorporation of CF 3–BCP motifs into oxindole frameworks and expands the accessible bioisosteric chemical space for drug discovery.

U2 - 10.1021/acs.orglett.5c04624

DO - 10.1021/acs.orglett.5c04624

M3 - Article

C2 - 41432245

SN - 1523-7060

VL - 28

SP - 248

EP - 253

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -