Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with <i>N</i>-selenocyanatophthalimide

Gao, Yong; Hua, Ruirui; Yin, Hengbo; Chen, Fuxue

doi:10.1039/d3qo00347g

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00347g

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Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

Yong Gao

Ruirui Hua

Hengbo Yin

et al.

Abstract: A visible-light-induced decarboxylative radical selenocyanation reaction of aliphatic carboxylic acids with the electrophilic N-selenocyanatophthalimide has been developed.

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2024

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Cited by 4 publications

References 40 publications

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Organophotocatalytic Remote Thiocyanation Reaction via Ring‐Opening Functionalization of Cycloalkanols

Hua,

Wang,

Yin

et al. 2024

Chemistry A European J

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The remote C(sp3)‐SCN bond formation via ring‐opening functionalization of cycloalkanols with N‐thiocyanatosaccharin as the precursor of SCN radicals and pyrylium salt as the organic photocatalyst under visible light has been developed. Thus, various terminal keto thiocyanates were prepared without transition metals and oxidants in moderate to good yields. The simplicity, wide substrate scope and mild conditions feature its synthetic application capability.

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Organophotocatalytic Remote Thiocyanation Reaction via Ring‐Opening Functionalization of Cycloalkanols

Hua,

Wang,

Yin

et al. 2024

Chemistry A European J

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Visible-Light-Driven Bifunctional Photocatalytic Radical-Cascade Selenocyanation/Cyclization of Acrylamides with KSeCN

Ren,

Zhang,

Wang

et al. 2024

J. Org. Chem.

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A visible-light-induced radical-cascade selenocyanation/cyclization of N-alkyl-N-methacryloyl benzamides, 2-aryl-N-acryloyl indoles, and N-methacryloyl-2-phenylbenzimidazoles with potassium isoselenocyanate (KSeCN) was developed. The reactions were carried out with inexpensive KSeCN as a selenocyanation reagent, potassium persulfate as an oxidant, 2,4,6-triphenylpyrylium tetrafluoroborate as a bifunctional catalyst for phase-transfer catalysis, and photocatalysis. A library of selenocyanate-containing isoquinoline-1,3(2H,4H)-diones, indolo[2,1-a]isoquinoline-6(5H)-ones, and benzimidazo[2,1-a]isoquinolin-6(5H)-ones were achieved in moderate to excellent yields at room temperature under visible-light and ambient conditions. Importantly, the present protocol features mild reaction conditions, large-scale synthesis, simple manipulation, product derivatization, good functional group, and heterocycle tolerance.

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Divergent process for the catalytic decarboxylative thiocyanation and isothiocyanation of carboxylic acids promoted by visible light

Vigier,

Gao,

Jubault

et al. 2024

Chem. Commun.

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Photocatalytic decarboxylative selenocyanation of 2-aryloxy and 2-aryl carboxylic acids with N-selenocyanatophthalimide

Abstract: A visible-light-induced decarboxylative radical selenocyanation reaction of aliphatic carboxylic acids with the electrophilic N-selenocyanatophthalimide has been developed.

Cited by 4 publications

References 40 publications

Organophotocatalytic Remote Thiocyanation Reaction via Ring‐Opening Functionalization of Cycloalkanols

Organophotocatalytic Remote Thiocyanation Reaction via Ring‐Opening Functionalization of Cycloalkanols

Visible-Light-Driven Bifunctional Photocatalytic Radical-Cascade Selenocyanation/Cyclization of Acrylamides with KSeCN

Divergent process for the catalytic decarboxylative thiocyanation and isothiocyanation of carboxylic acids promoted by visible light

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