Department of Pharmacy

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Author: search.filters.author.Chitkara, DeepakSubject: search.filters.subject.Synthesis

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    Synthesis of modified bile acids via palladium-catalyzed C(sp3)–H (hetero)arylation
    (RSC, 2023-07) Chitkara, Deepak; Sakhuja, Rajeev
    A Pd(II)-catalyzed strategy for the diastereo- and regioselective (hetero)arylation of unactivated C(sp3)–H bonds in bile acids is accomplished with aryl and heteroaryl iodides under solvent-free conditions using the 8-aminoquinoline auxiliary as a directing group. This methodology demonstrated excellent functional group tolerance with respect to aryl/heteroaryl iodides on O-protected N-(quinolin-8-yl)cholyl/deoxycholyl amides to afford β-C(sp3)–H (hetero)arylated products in good-to-excellent yields. Moreover, the 8-aminoquinoline (AQ) auxiliary can easily be removed to obtain modified bile acids.