In(OTf)3-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite

Sun, Jian-Ting; Li, Xin; Yang, Tianyu; Lv, Min; Chen, Ling‐Yan; Wei, Bang‐Guo

doi:10.1039/d2ob01196d

Cited by 5 publications

(1 citation statement)

References 59 publications

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“…This reaction most often consists of a CDC, forming a C–P bond from C–H and H–P bonds. This can be done using a range of metal catalysts such as copper, − iron, cobalt, , molybdenum, gold, , silver, − indium, and antimony, , in combination with a terminal oxidant such as oxygen to regenerate the catalyst. Alternatively, in an attempt to offer a more sustainable protocol, some groups have opted for metal-free options using additives like DDQ, − I 2, CBr 4 , diethyl azodicarboxylate, thiourea, , iminium cations, , ortho -quinone, or sulfuryl chloride to initiate the reaction.…”

Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

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The increasing importance of azaheterocyclic phosphonates in the agrochemical, synthetic, and medicinal field has provoked an intense search in the development of synthetic routes for obtaining novel members of this family of compounds. This updated review covers methodologies established since 2004, focusing on the synthesis of azaheterocyclic phosphonates, of which the phosphonate moiety is directly substituted onto to the azaheterocyclic structure. Emphasizing recent advances, this review classifies newly developed synthetic approaches according to the ring size and providing information on biological activities whenever available. Furthermore, this review summarizes information on various methods for the formation of C–P bonds, examining sustainable approaches such as the Michaelis–Arbuzov reaction, the Michaelis–Becker reaction, the Pudovik reaction, the Hirao coupling, and the Kabachnik–Fields reaction. After analyzing the biological activities and applications of azaheterocyclic phosphonates investigated in recent years, a predominant focus on the evaluation of these compounds as anticancer agents is evident. Furthermore, emerging applications underline the versatility and potential of these compounds, highlighting the need for continued research on synthetic methods to expand this interesting family.

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Section: Six-membered Rings: Nonaromatic Aromatic and Benzo-fused Het...mentioning

confidence: 99%

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Mayorquín-Torres,

Simoens,

Bonneure

et al. 2024

Chem. Rev.

View full text Add to dashboard Cite

show abstract

Recent progress in the direct phosphorylation of parent heterocycles to construct phosphorylated heterocycles

Zhong

Deng

Chen

2023

Chem Heterocycl Comp

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Facile InCl3-catalyzed room temperature synthesis and electrochemical behavior of ferrocene appended (R, S)-α-aminophosphonates

Anand,

Sivaramakrishna

2024

Journal of Molecular Structure

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In(OTf)₃-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite

Abstract: A practical approach to α-aminophosphonates has been developed through an In(OTf)3-catalyzed N-α phosphonylation of N,O-acetals with triethyl phosphite 7. Indoline and isoindoline N,O-acetals 6a-6j, 9a-9j and chain N,O-acetals 11a-11p were...

Cited by 5 publications

References 59 publications

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Synthetic Methods for Azaheterocyclic Phosphonates and Their Biological Activity: An Update 2004–2024

Recent progress in the direct phosphorylation of parent heterocycles to construct phosphorylated heterocycles

Facile InCl3-catalyzed room temperature synthesis and electrochemical behavior of ferrocene appended (R, S)-α-aminophosphonates

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