Pd-catalysed hydrodehalogenation of aryl chlorides: a mild method for deuteration and detoxification

Burhenn, Angela; Bavaro, Roberta; Gessner, Viktoria H.

doi:10.1039/d3cy00432e

“…The authors have cited additional references within the Supporting Information (Ref. [15][16][17][18][19][20][21][22][23][24][25][26][27]). The Supporting Information includes references to some compound MS(EI) data.…”

Section: Supporting Information Summarymentioning

confidence: 99%

Pd(OAc)₂/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Zhang,

Sang,

Wang

et al. 2023

ChemistrySelect

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Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

Qu,

Wan,

Zhang

et al. 2024

Angewandte Chemie

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The development of green and efficient deuteration methods is of great significance for various fields such as organic synthesis, analytical chemistry, and medicinal chemistry. Herein, we have developed a dehalogenative deuteration strategy using piezoelectric materials as catalysts in a solid‐phase system under ball‐milling conditions. This non‐spontaneous reaction is induced by mechanical force. D2O can serve as both a deuterium source and an electron donor in the transformation, eliminating the need for additional stoichiometric exogenous reductants. A series of (hetero)aryl iodides can be transformed into deuterated products with high deuterium incorporation. This method not only effectively overcomes existing synthetic challenges but can also be used for deuterium labelling of drug molecules and derivatives. Bioactivity experiments with deuterated drug molecule suggest that the D‐ipriflavone enhances the inhibitory effects on osteoclast differentiation of BMDMs in vitro.

show abstract

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

Qu,

Wan,

Zhang

et al. 2024

Angew Chem Int Ed

1

0

View full text Add to dashboard Cite

The development of green and efficient deuteration methods is of great significance for various fields such as organic synthesis, analytical chemistry, and medicinal chemistry. Herein, we have developed a dehalogenative deuteration strategy using piezoelectric materials as catalysts in a solid‐phase system under ball‐milling conditions. This non‐spontaneous reaction is induced by mechanical force. D2O can serve as both a deuterium source and an electron donor in the transformation, eliminating the need for additional stoichiometric exogenous reductants. A series of (hetero)aryl iodides can be transformed into deuterated products with high deuterium incorporation. This method not only effectively overcomes existing synthetic challenges but can also be used for deuterium labelling of drug molecules and derivatives. Bioactivity experiments with deuterated drug molecule suggest that the D‐ipriflavone enhances the inhibitory effects on osteoclast differentiation of BMDMs in vitro.

show abstract

Pd-catalysed hydrodehalogenation of aryl chlorides: a mild method for deuteration and detoxification

Abstract: (Poly)halogenated arenes are important electrophiles in organic synthesis but often also toxic and harmful to human health and the environment. Hydrodehalogenation represents a powerful method for detoxification, but usually requires...

Cited by 4 publications

References 72 publications

Pd(OAc)₂/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Pd(OAc)₂/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

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Pd-catalysed hydrodehalogenation of aryl chlorides: a mild method for deuteration and detoxification

Abstract: (Poly)halogenated arenes are important electrophiles in organic synthesis but often also toxic and harmful to human health and the environment. Hydrodehalogenation represents a powerful method for detoxification, but usually requires...

Cited by 4 publications

References 72 publications

Pd(OAc)2/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Pd(OAc)2/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

Mechanical‐Force‐Induced Non‐spontaneous Dehalogenative Deuteration of Aromatic Iodides Enabled by Using Piezoelectric Materials as a Redox Catalyst

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Product

Resources

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Pd(OAc)₂/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion

Pd(OAc)₂/Xantphos Catalyzed Reductive Coupling of Sulfonyl Chlorides: Synthesis of Thioethers by Sulphur Dioxide Extrusion