Photoinduced iron-catalyzed reduction of nitroarenes for multicomponent synthesis of α-branched secondary amines

Herein, we report a visible-light-induced, iron-catalyzed protocol that achieves <i>in situ</i> reduction of nitroarenes to anilines, followed by alkane C-H activation <i>via</i> a ligand-to-metal charge transfer (LMCT) pathway to furnish α-branched secondary amines under mild conditions. This one-pot, multicomponent strategy tolerates a wide range of nitroarenes, aldehydes, and alkanes, affording the desired products in good to excellent yields with broad functional group compatibility. Mechanistic investigations reveal that visible-light irradiation promotes efficient reduction of nitroarenes, while photoexcitation of Fe(III) species triggers LMCT to generate chlorine radicals, which engage in the subsequent three-component coupling.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc04672f
Primary Topic
Nanomaterials for catalytic reactions
Type
article
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article

Photoinduced iron-catalyzed reduction of nitroarenes for multicomponent synthesis of α-branched secondary amines

Ke Zheng, Huiji Gao, Qian Zhang
Chemical Communications
Nanomaterials for catalytic reactions
article

Photoinduced iron-catalyzed reduction of nitroarenes for multicomponent synthesis of α-branched secondary amines

Ke Zheng, Huiji Gao, Qian Zhang
article en

Abstract

Herein, we report a visible-light-induced, iron-catalyzed protocol that achieves <i>in situ</i> reduction of nitroarenes to anilines, followed by alkane C-H activation <i>via</i> a ligand-to-metal charge transfer (LMCT) pathway to furnish α-branched secondary amines under mild conditions. This one-pot, multicomponent strategy tolerates a wide range of nitroarenes, aldehydes, and alkanes, affording the desired products in good to excellent yields with broad functional group compatibility. Mechanistic investigations reveal that visible-light irradiation promotes efficient reduction of nitroarenes, while photoexcitation of Fe(III) species triggers LMCT to generate chlorine radicals, which engage in the subsequent three-component coupling.

Chemical CommunicationsVol. 61(84)
Sichuan University (CN), State Key Laboratory of Biotherapy
Openalex Percentile: Top 82%
Nanomaterials for catalytic reactions
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Photoinduced iron-catalyzed reduction of nitroarenes for multicomponent synthesis of α-branched secondary amines — Ke Zheng, Huiji Gao, et al. · Chemical Communications (2025) | TGRS Research Map | TGRS