Unactivated Alkyl Chloride Reactivity in Excited-State Palladium Catalysis

Krishnamoorthy Muralirajan; Rajesh Kancherla; Aidana Gimnkhan; Magnus Rueping

doi:10.1021/acs.orglett.1c02467

Unactivated Alkyl Chloride Reactivity in Excited-State Palladium Catalysis

Krishnamoorthy Muralirajan, Rajesh Kancherla, Aidana Gimnkhan, Magnus Rueping

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

57 Scopus citations

Abstract

Excited-state palladium catalysis is an efficient process for the alkylation of diverse organic compounds via the generation of alkyl radicals from alkyl bromides and iodides. However, the generation of alkyl radicals from more stable alkyl chlorides remains challenging. Herein, we demonstrate the excited-state palladium-catalyzed synthesis of oxindoles and isoquinolinediones via alkylation/annulation reaction by overcoming inherent limitations associated with unactivated C(sp3)-Cl bond activation at room temperature.

Original language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.1c02467
State	Published - Aug 25 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-08-31
Acknowledged KAUST grant number(s): URF/1/4025
Acknowledgements: We acknowledge King Abdullah University of Science and Technology (KAUST) for support. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4025).

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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title = "Unactivated Alkyl Chloride Reactivity in Excited-State Palladium Catalysis",

abstract = "Excited-state palladium catalysis is an efficient process for the alkylation of diverse organic compounds via the generation of alkyl radicals from alkyl bromides and iodides. However, the generation of alkyl radicals from more stable alkyl chlorides remains challenging. Herein, we demonstrate the excited-state palladium-catalyzed synthesis of oxindoles and isoquinolinediones via alkylation/annulation reaction by overcoming inherent limitations associated with unactivated C(sp3)-Cl bond activation at room temperature.",

author = "Krishnamoorthy Muralirajan and Rajesh Kancherla and Aidana Gimnkhan and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2021-08-31 Acknowledged KAUST grant number(s): URF/1/4025 Acknowledgements: We acknowledge King Abdullah University of Science and Technology (KAUST) for support. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4025).",

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month = aug,

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doi = "10.1021/acs.orglett.1c02467",

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journal = "Organic Letters",

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T1 - Unactivated Alkyl Chloride Reactivity in Excited-State Palladium Catalysis

AU - Muralirajan, Krishnamoorthy

AU - Kancherla, Rajesh

AU - Gimnkhan, Aidana

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2021-08-31 Acknowledged KAUST grant number(s): URF/1/4025 Acknowledgements: We acknowledge King Abdullah University of Science and Technology (KAUST) for support. This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (URF/1/4025).

PY - 2021/8/25

Y1 - 2021/8/25

N2 - Excited-state palladium catalysis is an efficient process for the alkylation of diverse organic compounds via the generation of alkyl radicals from alkyl bromides and iodides. However, the generation of alkyl radicals from more stable alkyl chlorides remains challenging. Herein, we demonstrate the excited-state palladium-catalyzed synthesis of oxindoles and isoquinolinediones via alkylation/annulation reaction by overcoming inherent limitations associated with unactivated C(sp3)-Cl bond activation at room temperature.

AB - Excited-state palladium catalysis is an efficient process for the alkylation of diverse organic compounds via the generation of alkyl radicals from alkyl bromides and iodides. However, the generation of alkyl radicals from more stable alkyl chlorides remains challenging. Herein, we demonstrate the excited-state palladium-catalyzed synthesis of oxindoles and isoquinolinediones via alkylation/annulation reaction by overcoming inherent limitations associated with unactivated C(sp3)-Cl bond activation at room temperature.

UR - http://hdl.handle.net/10754/670850

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.1c02467

U2 - 10.1021/acs.orglett.1c02467

DO - 10.1021/acs.orglett.1c02467

M3 - Article

C2 - 34432470

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Unactivated Alkyl Chloride Reactivity in Excited-State Palladium Catalysis

Abstract

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