Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

Research output: Contribution to journalArticleScientificpeer-review

Abstract

A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH(2), photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.
Original languageEnglish
JournalOrganic Letters
Volume21
Issue number10
Pages (from-to)3764–3768
Number of pages5
ISSN1523-7060
DOIs
Publication statusPublished - 8 May 2019
MoE publication typeA1 Journal article-refereed

Fields of Science

  • 116 Chemical sciences

Cite this

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title = "Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant",
abstract = "A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH(2), photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.",
keywords = "116 Chemical sciences",
author = "Aleksandar Todorov and Aikonen, {Santeri Alfred Arttu} and Mikko Muuronen and Juho Helaja",
year = "2019",
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day = "8",
doi = "10.1021/acs.orglett.9b01205",
language = "English",
volume = "21",
pages = "3764–3768",
journal = "Organic Letters",
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publisher = "American Chemical Society",
number = "10",

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Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant. / Todorov, Aleksandar; Aikonen, Santeri Alfred Arttu; Muuronen, Mikko; Helaja, Juho.

In: Organic Letters, Vol. 21, No. 10, 08.05.2019, p. 3764–3768.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

AU - Todorov, Aleksandar

AU - Aikonen, Santeri Alfred Arttu

AU - Muuronen, Mikko

AU - Helaja, Juho

PY - 2019/5/8

Y1 - 2019/5/8

N2 - A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH(2), photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.

AB - A photoreductive protocol utilizing [Ru(bpy)(3)](2+) photocatalyst, blue light LEDs, and ascorbic acid (AscH(2)) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH(2), photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.

KW - 116 Chemical sciences

U2 - 10.1021/acs.orglett.9b01205

DO - 10.1021/acs.orglett.9b01205

M3 - Article

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SP - 3764

EP - 3768

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

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