Selective Defluoroalkylation and Hydrodefluorination of Trifluoromethyl Groups Photocatalyzed by Dihydroacridine Derivatives

Li, Shi-Yu; Yang, Xin-Yu; Shen, Peng-Hui; Xu, Lei; Xu, Jun; Zhang, Qi; Xu, Hua-Jian

doi:10.1021/acs.joc.3c02135

Cited by 5 publications

(2 citation statements)

References 72 publications

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“…Recently, Xu's group achieved selective functionalization of CÀ F bonds in trifluoromethyl groups under mild conditions using dihydroacridine derivatives as photocatalysts (Scheme 4IV). [21] Mechanistic studies and DFT calculations revealed that dihydroacridine derivatives exhibited high reducibility under light irradiation and function as photocatalysts for reductive defluorination reactions. Additionally, this study provided valuable insights into the properties of dihydroacridine derivatives as photocatalysts, emphasizing the importance of maintaining planar conformations and large conjugated systems for optimal catalytic activity.…”

Section: Hydrodefluorination and Defluoroalkylationmentioning

confidence: 99%

Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

Liu,

Li,

et al. 2024

ChemCatChem

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The selective C‐F bonds functionalization in available trifluoromethyl compounds is an economic route for obtaining high‐value organic fluorine compounds. However, due to the high C‐F bonds dissociation energy in trifluoromethyl group, the strength of the bond decreases continuously during defluorination, posing a challenge in modifying such molecules without over‐conversion. Over the past few years, there has been significant progress in developing efficient methods for constructing difluoromethylene unit, using approaches such as radical chemistry, photochemistry, electrochemistry, and organometallic chemistry. These methods involve difluorocarbon radicals, difluorocarbon cations, difluorocarbon anions, and trifluoromethyl carbenes as intermediates. In this review, we summarized the recent five years of research achievements in this field for selective single C‐F bond cleavage in trifluoromethyl aromatic and carbonyl compounds to gain diverse difluoromethylene‐containing organic molecules via different intermediate strategies.

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Section: Hydrodefluorination and Defluoroalkylationmentioning

confidence: 99%

Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

Liu,

Li,

et al. 2024

ChemCatChem

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“…In particular, fluorinated heterocyclic compounds can be directly used as active fragments of drugs and functional materials, while others can be used as precursors of organic synthesis to obtain more valuable organic compounds by C–F bond activation reactions . Among them, monofluorinated heterocyclic compounds have attracted our attention because of their greater ability to functionalize C–F bonds …”

Section: Introductionmentioning

confidence: 99%

Unveiling the Selectivity of Ru(II)-Catalyzed C–H Activation for Defluorinative Cyclization of 2-Arylbenzimidazole and Trifluoromethyl Diazo: A DFT Study

Huang,

Sun,

Wang

et al. 2024

J. Org. Chem.

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The synthesis of monofluorinated heterocyclic compounds by C−H activation combined with defluorination is useful. Studies on the reaction mechanism and selectivity have shown that these processes play a positive role in promoting the development of monofluorinated reactions. Density functional theory (DFT) calculations were performed to investigate the mechanism and selectivity of Ru(II)-catalyzed 2-arylbenzimidazole with trifluoromethyl diazo. DFT calculations showed that C−H activation occurs through a concerted metalation/deprotonation (CMD) mechanism. After that, deprotonation and defluorinative cyclization are assisted by acetate and trifluoroethanol (TFE). Further mechanistic insights through noncovalent interaction (NCI) analysis were also obtained to elucidate the origin of the selectivity in the defluorination process.

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Visible light induced selective cleavage of single C(sp3)-F bond in trifluoromethyl groups containing compounds

Wang,

Wang

2024

Tetrahedron

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Selective Defluoroalkylation and Hydrodefluorination of Trifluoromethyl Groups Photocatalyzed by Dihydroacridine Derivatives

Cited by 5 publications

References 72 publications

Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

Recent Advance in the C−F Bond Functionalization of Trifluoromethyl Aromatic and Carbonyl Compounds

Unveiling the Selectivity of Ru(II)-Catalyzed C–H Activation for Defluorinative Cyclization of 2-Arylbenzimidazole and Trifluoromethyl Diazo: A DFT Study

Visible light induced selective cleavage of single C(sp3)-F bond in trifluoromethyl groups containing compounds

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