Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

Ding, Yuxuan; Luo, Shihui; Adijiang, Adila; Zhao, Hongye; An, Jie

doi:10.1021/acs.joc.8b01730

Cited by 34 publications

(15 citation statements)

References 38 publications

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“…An intriguing example was reported by An and co‐workers. They exploited sodium‐mediated electron transfer reactions for the synthesis of α,α‐dideutero amines in the presence sodium dispersions in EtOD−d1 …”

Section: Figurementioning

confidence: 99%

Continuous‐Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α‐Dideutero Amines

et al. 2019

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A simple and efficient continuous flow methodology has been developed for hydrogenation and reductive deuteration of nitriles to yield primary amines and also valuable α,α‐dideutero analogues. Raney nickel proved to be a useful catalyst for the transformation of a wide range of nitriles under reasonably mild conditions with excellent deuterium incorporation (>90 %) and quantitative conversion. Among known model compounds, three new deuterated primary amines were prepared. The large‐scale synthesis of deuterated tryptamine was also carried out to deliver 1.1 g product under flow conditions.

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Section: Figurementioning

confidence: 99%

Continuous‐Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α‐Dideutero Amines

et al. 2019

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“…The same group also reported the deuteration of aliphatic nitriles to give α,α-dideuterioamines, employing sodium dispersion (particle size 5-10 µm) as the electron donor, and ethanol-d1 as the deuterium source (Scheme 16). 40 This reaction was used for the synthesis of deuterated tryptamine and dopamine with 84% and 88% deuterium incorporation, respectively. bond of a carboxamide in a chemoselective manner by the use of sodium dispersion (particle size 5-10 µm) in hexane under N2 at 0 °C (Scheme 17).…”

Section: Scheme 15 Reductive Deuteration Of Terminal Alkynes With Sd and Ethanol-d1mentioning

confidence: 99%

Recent Advances in the Use of Sodium Dispersion for Organic Synthesis

De¹,

Asako²,

Ilies³

2021

Synthesis

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This short review describes the recent emergence of organosodium chemistry, motivated by the requirements of modern synthetic chemistry for sustainability, and powered by the use of sodium dispersion, a form of sodium that is commercially available, easy to handle, and has a large active surface area. We present recent preparation methods of oraganosodium compounds using sodium dispersion, and their applications to synthesis; sodium amides and phosphides are also briefly discussed.

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“…The original approach for the synthesis of deuterated compounds involves classical transformations with deuterated reagents, 14,15 deuterated starting materials, 16,17 or deuterated solvents, with reductive deuteration being one such example. [18][19][20] However, these strategies can be time-consuming and/or cost-intensive. Indeed, deuterated reagents are expensive and should be ideally introduced at the end of a synthesis to reduce losses.…”

Section: Introductionmentioning

confidence: 99%

40 Years of Hydrogen–Deuterium Exchange Adjacent to Heteroatoms: A Survey

Michelotti

Roche²

2019

Synthesis

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Deuteration of bioactive molecules is gaining more and more attention, especially after the approval of the first deuterated drug (Austedo™) by the US Food and Drug Administration (FDA). Not only is deuteration important for drug development, the amount of deuterium in a molecule is critical for the production of standards in mass spectrometry and the selectivity of the deuteration is mandatory for NMR applications. Very frequently, the molecules involved in these applications contain several heteroatoms. It has been demonstrated that oxygen-, nitrogen-, and more recently, sulfur-containing molecules can be easily deuterated at the α position leading to high deuterium incorporation. In this review we will focus our attention on the historical background and the recent progress made on heteroatom-directed deuteration, with particular attention on the catalysts and the mechanisms that drive such transformations.1 Introduction2 Oxygen-Directed Deuteration3 Nitrogen-Directed Deuteration4 Sulfur-Directed Deuteration5 Conclusion

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Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

Cited by 34 publications

References 38 publications

Continuous‐Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α‐Dideutero Amines

Continuous‐Flow Hydrogenation and Reductive Deuteration of Nitriles: a Simple Access to α,α‐Dideutero Amines

Recent Advances in the Use of Sodium Dispersion for Organic Synthesis

40 Years of Hydrogen–Deuterium Exchange Adjacent to Heteroatoms: A Survey

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