Visible Light Driven Oxidative Coupling of Amines and P(O)−H/P−OR Compounds under Photocatalyst‐Free Conditions

Fu, Ying; Duan, Fei; Du, Zhengyin

doi:10.1002/ajoc.202100052

Cited by 6 publications

(2 citation statements)

References 41 publications

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“…在该反应中, 有机染料玫瑰红作为光敏剂, 空气中的氧气作为氧化剂, 能够以中等至良好的产率获得一系列 S-P(O)偶联产物, 该反应表现出优异的化学选择性和良好的底物兼容性. 此外, 这种光催化的 Atherton-Todd-type 反应也同样适用于胺类底物 [45] .…”

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Recent Advances of the Atherton-Todd Reaction

Fang¹,

Liu²,

Wang³

2023

Chinese Journal of Organic Chemistry

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Phosphoramides or phosphates and their derivatives are a very important class of phosphorus-containing organic molecules, which are widely applied in medicinal chemistry, material chemistry and organic catalysis. As one of the most effective methods towards constructing phosphorus compounds, the Atherton-Todd reaction involves in situ halogenation of P(O)-H molecules with tetrachloromethane to generate the key intermediates of phosphoryl chlorides in the presence of bases, which subsequently react with amines or alcohols to form the corresponding phosphoramide or phosphate products. In recent years, this reaction has been widely explored by synthetic chemists due to its ease of operation, high atom economy, broad substrate versatility, and ease of incorporation of phosphorus units into active structural fragments. The research progress of the Atherton-Todd reaction and its application in organic synthesis in recent decades are summarized, and a brief outlook on the current research challenges is put forward, hoping to provide reference and thinking for the further development of the Atherton-Todd reaction.

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Recent Advances of the Atherton-Todd Reaction

Fang¹,

Liu²,

Wang³

2023

Chinese Journal of Organic Chemistry

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“…These methods disclose the tandem cyclization of N -propargylindoles with heteroatom centric radicals and a carbon-centered acyl radical, lacking the method for the cyclization of N -propargylindoles with carbon-centered alkyl radicals, especially oxoalkyl radicals. On the other hand, photocatalysis, as a mild and efficient catalytic strategy, has been widely used by organic chemists to construct a variety of molecules due to its economical and eco-friendly advantages …”

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confidence: 99%

Copper- and Visible-Light-Catalyzed Cascade Radical Cyclization of N-Propargylindoles with Cyclic Ethers

Wang

Ning

et al. 2022

J. Org. Chem.

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An efficient visible-light-assisted, copper-catalyzed tandem radical cyclization of N-propargylindoles with cyclic ethers is established. A series of 2-oxoalkyl-9H-pyrrolo[1,2-a]indol-9-ones with potential biological activities were synthesized in moderate yields by using a dual catalytic system with copper acetate as a transition metal catalyst and eosin Y as a visible light catalyst. The investigation of reaction mechanism shows that it goes through a cascade oxoalkyl radical addition, cyclization, and oxidation process.

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Palladium anchored on a covalent organic framework as a heterogeneous catalyst for phosphorylation of aryl bromides

Chen

Zhang

Xue

et al. 2021

Applied Organom Chemis

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A simple azine-linked covalent organic framework (COF) with high thermal and chemical stabilities has been prepared by using deep eutectic solvent (DES) as green media. The as-synthesized COF was employed as heterogeneous ligand for immobilization of Pd II . The obtained Pd-supported COF nanoparticles catalyst (defined as Pd/TFPT-Azine-COF) was found to be an efficient heterogeneous catalyst for the Hirao reaction of aryl halides and dialkyl phosphites or diphenylphosphine oxide with excellent recyclability, reusability, and retention of crystallinity.

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Visible Light Driven Oxidative Coupling of Amines and P(O)−H/P−OR Compounds under Photocatalyst‐Free Conditions

Cited by 6 publications

References 41 publications

Recent Advances of the Atherton-Todd Reaction

Recent Advances of the Atherton-Todd Reaction

Copper- and Visible-Light-Catalyzed Cascade Radical Cyclization of N-Propargylindoles with Cyclic Ethers

Palladium anchored on a covalent organic framework as a heterogeneous catalyst for phosphorylation of aryl bromides

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