Copper(II) Acetate‐Catalyzed Synthesis of Phosphorylated Pyridines <i>via</i> Denitrogenative C−P Coupling between Pyridotriazoles and P(O)H Compounds

Shen, Ruwei; Dong, Chao; Yang, Jianlin; Han, Li‐Biao

doi:10.1002/adsc.201800909

Cited by 32 publications

(21 citation statements)

References 73 publications

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“…Pyridotriazoles 1 were prepared by known methods. [17] H-phosphine oxides 2 a-2 g were prepared via similar procedures as reported in literatures. [18g] H-phosphonates 4, phenylphosphinic acid 7 and metal catalysts were purchased from commercial source and used as recieved.…”

Section: Methodsmentioning

confidence: 99%

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Rhodium‐Catalyzed O−H Bond Insertion Reaction between H‐Phosphoryl Compounds and 2‐Pyridyl Carbenes Generated from Pyridotriazoles

et al. 2021

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The dirhodium(II) tetraacetate-catalyzed OÀ H bond insertion reaction between H-phosphoryl compounds and 2pyridyl carbenes generated from pyridotriazoles is reported to afford a new synthesis of 2-picolyl phosphinates and phosphates in good to high yields with high selectivity. This new reaction represents a rare example showing a unique reactivity of the P(O)À H (vs POÀ H) functionality of Hphosphoryl compounds with respect to the insertion reactions of diazo compounds under transition metal catalysis.

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Section: Methodsmentioning

confidence: 99%

“…This is a knwon compound. [17] ( 4H),7.83 (d,J = 7.6 Hz,1H),2H),3H),4H),5.33 (d,J = 7.6 Hz, 2H); 13 129.8,129.1,128.7 (d,127.7,127.6,126.7,119.5,67.6 (d, J P-C = 6.4 Hz); 31 P NMR (160 MHz, CDCl 3 ) δ = 33.2. This is a knwon compound.…”

Section: Methodsmentioning

confidence: 99%

Rhodium‐Catalyzed O−H Bond Insertion Reaction between H‐Phosphoryl Compounds and 2‐Pyridyl Carbenes Generated from Pyridotriazoles

et al. 2021

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“…During our recent study on new synthetic methods towards organophosphorus compounds, [ 9,10 ] we came to consider that the relatively more available and stable α‐acyl‐α‐diazoacetates may undergo hydrolysis under suitable conditions to in‐situ form terminal diazoketones, which would be captured by H–heteroatom compounds upon transition metal catalysis leading to α‐functionalized ketones via the formation of C–heteroatom bond. [ 11 ] Accordingly, α‐acyl‐α‐diazoacetates may be regarded as convenient precursors of some labile (diazomethyl)ketones.…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Decarboxylative Hydrophosphinylation of α‐Acyl‐α‐Diazoacetates

et al. 2020

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A simple copper‐catalyzed decarboxylation–denitrogenation C–P coupling reaction of α‐acyl‐α‐diazoacetates with hydrophosphoryl compounds is reported. The reaction may proceed via a process involving the generation of (diazomethyl)ketones after hydrolysis in the presence of water and the hydrophosphinylation of the copper carbene intermediates. This finding may suggest the potential use of the relatively more readily available α‐acyl‐α‐diazoacetates as replacement of (diazomethyl)ketones in some cases.

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“…A Cu(II)-catalyzed denitrogenative C-P coupling reaction of pyridotriazoles 71 with P(O)H compounds 72 has been reported by Shen and co-workers (Scheme 21). 21 In this reaction, phosphorylmethyl pyridine derivatives 73 were obtained in modest to high yields. This method allows secondary phosphine oxides, H-phosphonates, and Hphosphinates to be involved in the reaction.…”

Section: Short Review Synthesis Scheme 20 Proposed Mechanisms For Thementioning

confidence: 99%

Recent Advances in Denitrogenative Reactions of Pyridotriazoles

Filippov¹,

Titov²,

Ростовский³

2020

Synthesis

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Diazo compounds display versatile reactivity and therefore are widely used in organic synthesis. Diazo compounds bearing a 2-pyridyl or a related azine moiety on the diazo carbon exist in the form of fused 1,2,3-triazoles. In this short review, we summarize the recent advances in denitrogenative reactions of [1,2,3]triazolo[1,5-a]pyridines (‘pyridotriazoles’) and related fused 1,2,3-triazoles. Over the past decade, there has been a surge of activity in this field, with novel denitrogenative reactions of pyridotriazoles induced by metal compounds, light, and Brønsted and Lewis acids having been devised. As a result, heterocyclic compounds and functionalized α-picolines as well as bioactive molecules have been synthesized. In the review, emphasis is also placed on the mechanisms of the new reactions.1 Introduction2 Ring-Chain Isomerization of Pyridotriazoles3 Metal-Catalyzed Reactions3.1 Rh(II) Catalysis3.2 Rh(III) Catalysis3.3 Cu Catalysis3.4 Pd Catalysis3.5 Catalysis by Other Metals4 Metal-Free Reactions5 Conclusion

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Copper(II) Acetate‐Catalyzed Synthesis of Phosphorylated Pyridines via Denitrogenative C−P Coupling between Pyridotriazoles and P(O)H Compounds

Cited by 32 publications

References 73 publications

Rhodium‐Catalyzed O−H Bond Insertion Reaction between H‐Phosphoryl Compounds and 2‐Pyridyl Carbenes Generated from Pyridotriazoles

Rhodium‐Catalyzed O−H Bond Insertion Reaction between H‐Phosphoryl Compounds and 2‐Pyridyl Carbenes Generated from Pyridotriazoles

Copper‐Catalyzed Decarboxylative Hydrophosphinylation of α‐Acyl‐α‐Diazoacetates

Recent Advances in Denitrogenative Reactions of Pyridotriazoles

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