Iridium‐Catalyzed H/D Exchange

Krüger, Jens; Manmontri, Boripont; Fels, Gregor

doi:10.1002/ejoc.200400669

Cited by 43 publications

(19 citation statements)

References 16 publications

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“…[16] In the area of homogeneous catalysis, Fels et al showed that a,b-unsaturated carboxylic acid derivatives can undergo H/ D exchange reactions at the b-position with D 2 O in the presence of IrA C H T U N G T R E N N U N G (COD)A C H T U N G T R E N N U N G (acac) (2 mmol%, 90 8C), presumably through cyclometallated intermediates. [17] Matsubara et al demonstrated that cyclic olefins such as cyclohexene and cyclodecene can undergo H/D exchange with D 2 O under irradiation of microwaves in the presence of RuCl 2 A C H T U N G T R E N N U N G (PPh 3 ) 3 (5 mol%, 140 8C, 0.34 MPa).…”

Section: Introductionmentioning

confidence: 99%

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Tse¹,

Xue²,

Lin³

et al. 2010

Adv Synth Catal

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Section: Introductionmentioning

confidence: 99%

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Tse¹,

Xue²,

Lin³

et al. 2010

Adv Synth Catal

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“…Mioskowski's group reported that 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) showed to be an isotope exchange catalyst in CDCl 3 at room temperature toward ketones and other acidic substrates 3e . Although other methods for deuteration of ketones are available, such as using the Pd/C‐H 2 ‐D 2 O system, other catalysts such as calcium vanadate apatite, antibody 38C2, cyclooctadieneiridium(I) acetylacetonate, Ir‐NHC complexes, and Pd/C utilizing NaBD 4 for catalyst activation were also used. Eames's group indicated that the regioselective C ‐deuteration of a series of related acyclic and exocyclic enolates derived from substituted aryl ketones .…”

Section: Introductionmentioning

confidence: 99%

A simple method for α‐position deuterated carbonyl compounds with pyrrolidine as catalyst

Zhan

Zhang

Huang

et al. 2014

Labelled Comp Radiopharmac

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A simple, cost-effective method for deuteration of carbonyl compounds employing pyrrolidine as catalyst and D2O as deuterium source was described. High degree of deuterium incorporation (up to 99%) and extensive functional group tolerance were achieved. It is the first time that secondary amines are used as catalysts for H/D exchange of carbonyl compounds, which also allow the deuteration of complex pharmaceutically interesting substrates. A possible catalytic mechanism, based on the hydrolysis of 1-pyrrolidino-1-cyclohexene, for this pyrrolidine-catalyzed H/D exchange reaction has been proposed.

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“…High reactivity and possibility to tune catalytic system by choosing ligands and solvent enable deuteration of α,β‐unsaturated carbonyl. For example, crotonic and cinnamic acids undergo deuteration at β‐position to carboxyl group with quantitative yield …”

Section: Fundamentals For Mechanism Of the Isotopic Exchange Reactionmentioning

confidence: 99%

Hydrogen/deuterium exchange in mass spectrometry

Kostyukevich

Acter

Zherebker

et al. 2018

Mass Spectrometry Reviews

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The isotopic exchange approach is in use since the first observation of such reactions in 1933 by Lewis. This approach allows the investigation of the pathways of chemical and biochemical reactions, determination of structure, composition, and conformation of molecules. Mass spectrometry has now become one of the most important analytical tools for the monitoring of the isotopic exchange reactions. Investigation of conformational dynamics of proteins, quantitative measurements, obtaining chemical, and structural information about individual compounds of the complex natural mixtures are mainly based on the use of isotope exchange in combination with high resolution mass spectrometry. The most important reaction is the Hydrogen/Deuterium exchange, which is mainly performed in the solution. Recently we have developed the approach allowing performing of the Hydrogen/Deuterium reaction on-line directly in the ionization source under atmospheric pressure. Such approach simplifies the sample preparation and can accelerate the exchange reaction so that certain hydrogens that are considered as non-labile will also participate in the exchange. The use of in-ionization source H/D exchange in modern mass spectrometry for structural elucidation of molecules serves as the basic theme in this review. We will focus on the mechanisms of the isotopic exchange reactions and on the application of in-ESI, in-APCI, and in-APPI source Hydrogen/Deuterium exchange for the investigation of petroleum, natural organic matter, oligosaccharides, and proteins including protein-protein complexes. The simple scenario for adaptation of H/D exchange reactions into mass spectrometric method is also highlighted along with a couple of examples collected from previous studies.

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Iridium‐Catalyzed H/D Exchange

Abstract: The scope and limitation of an iridium-catalysed H/D exchange reaction has been investigated. Our results suggest a general mechanism for specific labelling at aromatic and non-aromatic double bonds by D 2 O if an electron-donating

Cited by 43 publications

References 16 publications

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydrido‐ tris(triphenylphosphine)ruthenium(II) Complex

A simple method for α‐position deuterated carbonyl compounds with pyrrolidine as catalyst

Hydrogen/deuterium exchange in mass spectrometry

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