ArticleNature catalysis2019
Practical Synthesis of C-1 Deuterated Aldehydes Enabled by NHC Catalysis.
Article in Nature catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
25 citing papers in PubMed, 118 citations in OpenAlex.
- Photocatalyst-free photochemical deuteration via H/D exchange with DNature communications · 2025Article
- Boosted high-throughput D⁺ transfer from D₂O to unsaturated bonds via PdNature communications · 2025Article
- Desymmetric esterification catalysed by bifunctional chiral N-heterocyclic carbenes provides access to inherently chiral calix[4]arenes.Nature communications · 2025Article
- Paired Electrosynthesis at Interdigitated Microband Array Electrodes without Intentionally Added Electrolyte: C-C Coupling of Dicyanobenzenes with Methanol.The journal of physical chemistry. C, Nanomaterials and interfaces · 2025Article
- Organophotocatalytic Selective Deuteration of Metabolically Labile Heteroatom Adjacent C-H Bonds via H/D Exchange with DOrganic letters · 2024Article
- Organophotocatalytic α-deuteration of unprotected primary aminesChemical communications (Cambridge, England) · 2024Article
- Deuterated reagents in multicomponent reactions to afford deuterium-labeled products.Beilstein journal of organic chemistry · 2024Article
- Deuterated Drugs and Biomarkers in the COVID-19 Pandemic.ACS omega · 2022Review
- Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides.Nature communications · 2022Article
- Highly selective single and multiple deuteration of unactivated C(spNature communications · 2022Article
- Realizing 1,1-Dehydration of Secondary Alcohols to Carbenes: Pyrrolidin-2-ols as a Source of Cyclic (Alkyl)(Amino)Carbenes.Angewandte Chemie (International ed. in English) · 2022Article
- Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives.Chemical science · 2022Article
- The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights.The Journal of organic chemistry · 2022Article
- Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.Angewandte Chemie (International ed. in English) · 2022Article
- Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides.Chemical science · 2021Article
- Selective oxidation of alcohol-RSC advances · 2021Article
- Article
- Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides.Nature communications · 2021Article
- Hybrid Chemo-, Bio-, and Electrocatalysis for Atom-Efficient Deuteration of Cofactors in Heavy Water.ACS catalysis · 2021Article
Corrections and comments
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
The recent surge in applications of deuterated pharmaceutical agents has created an urgent demand for synthetic methods that efficiently generate deuterated building blocks. Here we show that N-heterocyclic carbenes (NHC) promote a reversible hydrogen-deuterium exchange (HDE) reaction with simple aldehydes, which leads to a practical approach to synthetically valuable C-1 deuterated aldehydes. The reactivity of the well-established NHC catalysed formation of Breslow intermediates from aldehydes is reengineered to overcome the overwhelmingly kinetically favorable, irreversible benzoin condensation reaction and achieve the critical reversibility to drive the formation of desired deuterated products when an excess of D
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.