Nickel‐Photoredox‐Catalyzed Synthesis of sp2−sp3 Fragments and the Impact of Bicycloalkane Isosteric Replacement on Their Physical‐Chemical Properties

Bicycloalkanes are well‐known isosteres of alkynes and aromatic rings and their use in the field of medicinal chemistry and drug discovery has been on the rise in the past ten years. Herein, we report the modular and practical synthesis of bicycloalkane‐containing fragments using nickel‐photoredox c...

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Bibliographic Details
Published in:Helvetica chimica acta 2023-04, Vol.106 (4), p.n/a
Main Authors: Lefebvre, Quentin, Bocu, Mina, Giorgiutti, Christophe, Fessard, Thomas C.
Format: Article
Language:English
Subjects:
Alkynes
aqueous solubility
Aromatic compounds
Catalysis
Chemical properties
Chemical synthesis
Fragments
isosteres
medicinal chemistry
Nickel
Pentane
photochemistry
Photoredox catalysis
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Summary:Bicycloalkanes are well‐known isosteres of alkynes and aromatic rings and their use in the field of medicinal chemistry and drug discovery has been on the rise in the past ten years. Herein, we report the modular and practical synthesis of bicycloalkane‐containing fragments using nickel‐photoredox catalysis. The comparison of their relevant physical‐chemical properties with their aromatic counterparts shows a substantial improvement in LogP and aqueous solubility for bicyclo[1.1.1]pentane derivatives, but not for bicyclo[2.2.2]octane derivatives.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.202200189