Facile and practical hydrodehalogenations of organic halides enabled by calcium hydride and palladium chloride

Gui, Jingjing; Cai, Xin; Chen, Lingyun; Zhou, Yuxin; Zhu, Wenjing; Jiang, Yuanrui; Hu, Min; Chen, Xiaobei; Hu, Yan‐Wei; Zhang, Shilei

doi:10.1039/d1qo00758k

Cited by 10 publications

(1 citation statement)

References 100 publications

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“…Traditionally, sodium hydride (NaH) is employed as a Brønsted base for deprotonation of acidic substrates. Our group has revealed that NaH could be activated as a reductant under the catalysis of palladium salt, to achieve a series of reduction reactions including debenzylation and deallylation, 25a 1,4-conjugate reductions of α,β-unsaturated carbonyl compounds, 25b and hydrodehalogenations of organic halides 25c (Scheme 1b ). As our continuing work in this area, we report herein the reduction of several kinds of N -heteroarenes through transfer hydrogenation with the NaH/Pd reductive system.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

et al. 2022

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An efficient and convenient palladium-catalyzed reductive system by employing sodium hydride as the hydrogen donor and acetic anhydride as an activator has been developed for transfer hydrogenation and acetylation of a wide range of N-heteroarenes including quinoline, phthalazine, quinoxaline, phenazine, phenanthridine and indole. Moreover, acridine substrates could be directly reduced without the use of acetic anhydride. This protocol provides a simple method for preparation of various saturated N-heterocycles.

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Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

et al. 2022

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The Reaction of Aryl Thiols or Thioureas with o‐Diiodoarenes/NaH to Access o‐Iodoaryl Thioethers

Hu,

Liu,

Liu

et al. 2024

Adv Synth Catal

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Herein we report a method for the synthesis of thioethers by forging C(aryl)‐S bond via an aryne mechanism. The active aryne species can be generated from o‐diiodoarenes and NaH in THF at room temperature, then lead to the arylations of a wide range of aryl thiols and thioureas. Different from transition metal‐catalyzed cross‐coupling reactions, no disubstituted byproduct is formed in our protocol. The o‐iodoaryl thioether products are intermediates that could be transformed into pharmaceutically interesting molecules.

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Manganese‐Catalyzed Transfer Hydrodebromination of Aryl Bromides with Ethanol

et al. 2023

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A convenient PNP pincer manganese catalyzed transfer hydrogenation of bromides to corresponding debrominated aryl compounds using ethanol as the hydrogen sources is reported. Importantly, the application of biomass-derived ethanol highlights the sustainability of the methodology. The use of 6phenyl substituted triazine-based P ipr N 5 P ipr manganese pincer catalyst allows for the debromination of various aryl bromides with good yields. Notably, the process also occurs with bromides derived from several classes of natural products and bioactive compounds, such as citronellol, diacetone fructose, cholesterol, and vitamin E.

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Facile and practical hydrodehalogenations of organic halides enabled by calcium hydride and palladium chloride

Abstract: Herein, a convenient hydrodehalogenation method was described by employing less-explored calcium hydride as the reductant. A wide range of organic halides such as aromatic bromides, aromatic chlorides, aromatic triflates, aliphatic...

Cited by 10 publications

References 100 publications

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

Palladium-Catalyzed Transfer Hydrogenation and Acetylation of N-Heteroarenes with Sodium Hydride as the Reductant

The Reaction of Aryl Thiols or Thioureas with o‐Diiodoarenes/NaH to Access o‐Iodoaryl Thioethers

Manganese‐Catalyzed Transfer Hydrodebromination of Aryl Bromides with Ethanol

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