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Highly selective catalytic transfer hydrodeuteration of cyclic alkenes
Hintzsche, Samuel J. ; Vang, Zoua Pa ; Rivera Torres, Emanuel , et al. J. Labelled Compd. Rad.,2023,66(3):86-94. DOI: 10.1002/jlcr.4015 PubMed ID: 36772856
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Abstract: Selective deuterium installation into small molecules is becoming increasingly desirable not only for the elucidation of mechanistic pathways and studying biological processes but also because of deuterium's ability to favorably adjust the pharmacokinetic parameters of bioactive molecules. Fused bicyclic moieties, especially those containing heteroatoms, are prevalent in drug discovery and pharmaceuticals. Herein, we report a copper-catalyzed transfer hydrodeuteration of cyclic and heterocyclic alkenes, which enables the synthesis of chromans, quinolinones, and tetrahydronaphthalenes that are precisely deuterated at the benzylic position. We also demonstrate the ability to place one deuterium atom at the homobenzylic site of these scaffolds with high regioselectivity by swapping transfer reagents for their isotopic analogs. Furthermore, examples of chemoselective transfer hydrogenation and transfer deuteration are disclosed, allowing for the simultaneous incorporation of two vicinal hydrogen or deuterium atoms into a double bond.
Keywords: copper ; deuteration ; hydrodeuteration ; hydrogenation ; transition metal catalysis
Purchased from AmBeed: 6836-19-7 ; 14243-64-2 ; 19315-93-6 ; 1810-66-8 ; 584-08-7 ; 189114-61-2 ; 447-53-0
CAS No. : | 19315-93-6 | MDL No. : | MFCD00239446 |
Formula : | C9H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AQLYZDRHNHZHIS-UHFFFAOYSA-N |
M.W : | 161.16 | Pubchem ID : | 177065 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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