Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates. / Pedersen, Stephan Korsgaard; Clementson, Sebastian; Kristensen, Jesper Langgaard; Jessing, Mikkel; El-Chami, Kassem.

In: Chemistry: A European Journal, Vol. 29, No. 35, e202300265, 2023.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Pedersen, SK, Clementson, S, Kristensen, JL, Jessing, M & El-Chami, K 2023, 'Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates', Chemistry: A European Journal, vol. 29, no. 35, e202300265. https://doi.org/10.1002/chem.202300265

APA

Pedersen, S. K., Clementson, S., Kristensen, J. L., Jessing, M., & El-Chami, K. (2023). Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates. Chemistry: A European Journal, 29(35), [e202300265]. https://doi.org/10.1002/chem.202300265

Vancouver

Pedersen SK, Clementson S, Kristensen JL, Jessing M, El-Chami K. Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates. Chemistry: A European Journal. 2023;29(35). e202300265. https://doi.org/10.1002/chem.202300265

Author

Pedersen, Stephan Korsgaard ; Clementson, Sebastian ; Kristensen, Jesper Langgaard ; Jessing, Mikkel ; El-Chami, Kassem. / Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates. In: Chemistry: A European Journal. 2023 ; Vol. 29, No. 35.

Bibtex

@article{55b1985f76f74255bb6c3e8e5c5d70c3,
title = "Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates",
abstract = "Here in we report on the decarboxylative alkenylation between alkyl carboxylic acids and enol triflates. The reaction is mediated by a dual catalytic nickel and iridium system, operating under visible light irradiation. Two competing catalytic pathways, from the excited state iridium photocatalyst, are identified. One is energy transfer from the excited state, resulting in formation of an undesired enol ester. The desired pathway involves electron transfer, resulting in decarboxylation to ultimately give the target product. The use of a highly oxidizing iridium photocatalyst is essential to control the reactivity. A diverse array of enol triflates and alkyl carboxylic acids are investigated, providing both scope and limitations of the presented methodology.",
author = "Pedersen, {Stephan Korsgaard} and Sebastian Clementson and Kristensen, {Jesper Langgaard} and Mikkel Jessing and Kassem El-Chami",
note = "{\textcopyright} 2023 Wiley-VCH GmbH.",
year = "2023",
doi = "10.1002/chem.202300265",
language = "English",
volume = "29",
journal = "Chemistry: A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "35",

}

RIS

TY - JOUR

T1 - Overcoming Energy Transfer for the Metallophotoredox Catalyzed Decarboxylative Alkenylation between Alkylcarboxylic Acids and Enol Triflates

AU - Pedersen, Stephan Korsgaard

AU - Clementson, Sebastian

AU - Kristensen, Jesper Langgaard

AU - Jessing, Mikkel

AU - El-Chami, Kassem

N1 - © 2023 Wiley-VCH GmbH.

PY - 2023

Y1 - 2023

N2 - Here in we report on the decarboxylative alkenylation between alkyl carboxylic acids and enol triflates. The reaction is mediated by a dual catalytic nickel and iridium system, operating under visible light irradiation. Two competing catalytic pathways, from the excited state iridium photocatalyst, are identified. One is energy transfer from the excited state, resulting in formation of an undesired enol ester. The desired pathway involves electron transfer, resulting in decarboxylation to ultimately give the target product. The use of a highly oxidizing iridium photocatalyst is essential to control the reactivity. A diverse array of enol triflates and alkyl carboxylic acids are investigated, providing both scope and limitations of the presented methodology.

AB - Here in we report on the decarboxylative alkenylation between alkyl carboxylic acids and enol triflates. The reaction is mediated by a dual catalytic nickel and iridium system, operating under visible light irradiation. Two competing catalytic pathways, from the excited state iridium photocatalyst, are identified. One is energy transfer from the excited state, resulting in formation of an undesired enol ester. The desired pathway involves electron transfer, resulting in decarboxylation to ultimately give the target product. The use of a highly oxidizing iridium photocatalyst is essential to control the reactivity. A diverse array of enol triflates and alkyl carboxylic acids are investigated, providing both scope and limitations of the presented methodology.

U2 - 10.1002/chem.202300265

DO - 10.1002/chem.202300265

M3 - Journal article

C2 - 36972020

VL - 29

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 35

M1 - e202300265

ER -

ID: 342612417