A direct fixation of CO<sub>2</sub> for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes

Bow, John-Paul J.; Adami, Valentina; Marasco, Agostino; Grønnevik, Gaute; Rivers, Dean A; Alvaro, Guiseppe; Riss, Patrick J.

doi:10.1039/d2cc01754g

Chem. Commun.

2022

DOI: 10.1039/d2cc01754g

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A direct fixation of CO₂ for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes

John-Paul J. Bow

Valentina Adami

Agostino Marasco

et al.

Abstract: Herein, we report a method for the isotopic labelling of hydantoins directly from CO2 by means of trimethyl-λ5-phosphine diiodide mediated carbonyl insertion. The method is suitable for 13C-labelling of diverse...

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“…The following supporting information can be downloaded at: , the corresponding Cartesian coordinates in DFT studies, copies of NMR spectra for all new compounds, and a reference list for the characterization data of all known compounds [ 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 ].…”

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Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Wang

Luo

et al. 2022

Molecules

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Conventional Staudinger reductions of organic azides are sluggish with aryl or bulky aliphatic azides. In addition, Staudinger reduction usually requires a large excess of water to promote the decomposition of the aza-ylide intermediate into phosphine oxide and amine products. To overcome the challenges above, we designed a novel triaryl phosphine reagent 2c with an ortho-SO2NH2 substituent. Herein, we report that such phosphine reagents are able to mediate the Staudinger reduction of both aryl and alkyl azides in either anhydrous or wet solvents. Good to excellent yields were obtained in all cases (even at a diluted concentration of 0.01 M). The formation of B-TAP, a cyclic aza-ylide, instead of phosphine oxide, eliminates the requirement of water in the Staudinger reduction. In addition, computational studies disclose that the intramolecular protonation of the aza-ylide by the ortho-SO2NH2 group is kinetically favorable and responsible for the acceleration of Staudinger reduction of the aryl azides.

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confidence: 99%

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Wang

Luo

et al. 2022

Molecules

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Synthesis, Molecular Docking, and Biological Evaluation of Pyridin-3-yl-Pyrimidin-2-yl-Triazole Derivatives as Anti-cancer Agents

Firoozpour

Moghimi

Barzegar

et al. 2023

Polycyclic Aromatic Compounds

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Organocatalysis for the Chemical Fixation of Carbon Dioxide to Synthesise N-Heterocycles

Esteves,

Morais Costa,

Tomazett

et al. 2024

CGC

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Organocatalysed reactions are becoming powerful tools in the construction of complex molecular skeletons. It gains extra importance when used as a chemical approach to the chemical fixation of carbon dioxide (CO2). Carbon dioxide is an increasingly dangerous environmental hazard as the global climate temperature rises through the greenhouse effect. Meanwhile, in the past decades, significant advances can be noted in the use of organocatalysis for CO2 capture and its conversion into valuable chemicals. Therefore, herein we review a full set of organocatalysts used in CO2 fixation for the synthesis of N-heterocycles since they are present in several chemical structures with biological relevance.

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A direct fixation of CO₂ for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes

Abstract: Herein, we report a method for the isotopic labelling of hydantoins directly from CO2 by means of trimethyl-λ5-phosphine diiodide mediated carbonyl insertion. The method is suitable for 13C-labelling of diverse...

Cited by 3 publications

References 36 publications

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Synthesis, Molecular Docking, and Biological Evaluation of Pyridin-3-yl-Pyrimidin-2-yl-Triazole Derivatives as Anti-cancer Agents

Organocatalysis for the Chemical Fixation of Carbon Dioxide to Synthesise N-Heterocycles

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A direct fixation of CO2 for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes

Abstract: Herein, we report a method for the isotopic labelling of hydantoins directly from CO2 by means of trimethyl-λ5-phosphine diiodide mediated carbonyl insertion. The method is suitable for 13C-labelling of diverse...

Cited by 3 publications

References 36 publications

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Ortho-Phosphinoarenesulfonamide-Mediated Staudinger Reduction of Aryl and Alkyl Azides

Synthesis, Molecular Docking, and Biological Evaluation of Pyridin-3-yl-Pyrimidin-2-yl-Triazole Derivatives as Anti-cancer Agents

Organocatalysis for the Chemical Fixation of Carbon Dioxide to Synthesise N-Heterocycles

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Product

Resources

About

A direct fixation of CO₂ for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes