Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates

Maxim Ratushnyy; Nikita Kvasovs; Sumon Sarkar; Vladimir Gevorgyan

doi:10.1002/anie.201915962

Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates

Maxim Ratushnyy, Nikita Kvasovs, Sumon Sarkar, Vladimir Gevorgyan

Research output: Contribution to journal › Article › peer-review

79 Scopus citations

Abstract

A mild visible-light-induced Pd-catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp²)−O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.

Original language	English (US)
Pages (from-to)	10316-10320
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	26
DOIs	https://doi.org/10.1002/anie.201915962
State	Published - Jun 22 2020

Keywords

homolysis
light-mediated reactions
palladium
radicals
triflates

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201915962

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title = "Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates",

abstract = "A mild visible-light-induced Pd-catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp2)−O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.",

keywords = "homolysis, light-mediated reactions, palladium, radicals, triflates",

author = "Maxim Ratushnyy and Nikita Kvasovs and Sumon Sarkar and Vladimir Gevorgyan",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates

AU - Ratushnyy, Maxim

AU - Kvasovs, Nikita

AU - Sarkar, Sumon

AU - Gevorgyan, Vladimir

PY - 2020/6/22

Y1 - 2020/6/22

N2 - A mild visible-light-induced Pd-catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp2)−O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.

AB - A mild visible-light-induced Pd-catalyzed intramolecular C−H arylation of amides is reported. The method operates by cleavage of a C(sp2)−O bond, leading to hybrid aryl Pd-radical intermediates. The following 1,5-hydrogen atom translocation, intramolecular cyclization, and rearomatization steps lead to valuable oxindole and isoindoline-1-one motifs. Notably, this method provides access to products with readily enolizable functional groups that are incompatible with traditional Pd-catalyzed conditions.

KW - homolysis

KW - light-mediated reactions

KW - palladium

KW - radicals

KW - triflates

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AN - SCOPUS:85083165958

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SP - 10316

EP - 10320

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 26

ER -

Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates

Abstract

Keywords

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