Light-induced ligand-to-metal charge transfer of Fe(<scp>iii</scp>)-OR species in organic synthesis

Qin, Jie; Lei, Hong; Gao, Chuanhua; Zheng, Yuewen; Zhao, Yating; Xia, Wujiong

doi:10.1039/d4ob00876f

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00876f

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Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Jie Qin,

Hong Lei,

Chuanhua Gao

et al.

Abstract: Light-induced ligand-to-metal charge transfer (LMCT) has been utilized as a powerful strategy in various organic reactions. First-row transition metals, especially iron complexes, show good applications in this process. Fe(III)-Cl and...

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Cited by 5 publications

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Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Zhu,

Bao,

Zhang

et al. 2024

J. Org. Chem.

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Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Zhu,

Bao,

Zhang

et al. 2024

J. Org. Chem.

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Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

Golagani,

Prakash,

Thapa

et al. 2024

Org. Lett.

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A novel photoinduced Fe(OTf)2/2,4,6-collidine-catalyzed alkylation of Morita–Baylis–Hillman (MBH) acetates using carboxylic acids in a regio- and stereoselective manner is reported. This method demonstrates a broad scope, encompassing various carboxylic acids and MBH acetates, including drugs and bioactive molecules, to synthesize densely functionalized cinnamates and acrylates. The reactions are performed in the green solvent dimethyl carbonate under oxidant-free conditions. Based on control experiments, a plausible mechanism involving an Fe(II)–Fe(III)–Fe(II) cycle is proposed.

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Synthesis of Alkyl Bis(trifluoromethyl)carbinols via Fe-LMCT-Enabled Hydrobis(trifluoromethyl)carbinolation of Alkenes

Guo,

Lai,

et al. 2024

Org. Lett.

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Bis(trifluoromethyl)carbinols are valuable pharmacophores, yet their synthesis is challenging, largely due to a scarcity of safe and effective bis(trifluoromethyl)carbinolation reagents. Here, we realized the hydrobis(trifluoromethyl)carbinolation of alkenes, utilizing stable and readily accessible 2,2-bis(trifluoromethyl)glycolic acid as a source of both the bis(trifluoromethyl)carbinol unit and a hydrogen atom. This process leverages a photoinduced Fe-LMCT-enabled radical decarboxylation process that generates a key bis(trifluoromethyl)carbinol radical intermediate. Our mild protocol facilitates the synthesis of a diverse range of alkyl bis(trifluoromethyl)carbinols, including structurally complex molecules with pharmaceutical relevance.

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Light-induced ligand-to-metal charge transfer of Fe(iii)-OR species in organic synthesis

Abstract: Light-induced ligand-to-metal charge transfer (LMCT) has been utilized as a powerful strategy in various organic reactions. First-row transition metals, especially iron complexes, show good applications in this process. Fe(III)-Cl and...

Cited by 5 publications

References 54 publications

Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Visible-Light Induced and Iron Peroxo-Promoted Radical Difunctionalization of Alkene for the Synthesis of β-Ketosulfone and α-Chloroketone

Visible-Light-Promoted Iron(II)/Lewis Base Catalysis for the Alkylation of Morita–Baylis–Hillman Acetates Using Carboxylic Acids

Synthesis of Alkyl Bis(trifluoromethyl)carbinols via Fe-LMCT-Enabled Hydrobis(trifluoromethyl)carbinolation of Alkenes

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