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1 article(s) from Son, Jongwoo

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

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Graphical Abstract

Scheme 1: Mn-catalyzed late-stage fluorination of sclareolide (1) and complex steroid 3.

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Figure 1: Proposed reaction mechanism of C–H fluorination by a manganese porphyrin catalyst.

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Scheme 2: Late-stage radiofluorination of biologically active complex molecules.

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Figure 2: Proposed mechanism of C–H radiofluorination.

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Scheme 3: Late-stage C–H azidation of bioactive molecules. ^a1.5 mol % of Mn(TMP)Cl (5) was used. ^bMethyl acet...

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Figure 3: Proposed reaction mechanism of manganese-catalyzed C–H azidation.

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Scheme 4: Mn-catalyzed late-stage C–H azidation of bioactive molecules via electrophotocatalysis. ^a2.5 mol % ...

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Figure 4: Proposed reaction mechanism of electrophotocatalytic azidation.

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Scheme 5: Manganaelectro-catalyzed late-stage azidation of bioactive molecules.

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Figure 5: Proposed reaction pathway of manganaelectro-catalyzed late-stage C–H azidation.

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Scheme 6: Mn-catalyzed late-stage amination of bioactive molecules. ^a3 Å MS were used. Protonation with HBF₄⋅...

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Figure 6: Proposed mechanism of manganese-catalyzed C–H amination.

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Scheme 7: Mn-catalyzed C–H methylation of heterocyclic scaffolds commonly found in small-molecule drugs. ^aDAS...

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Scheme 8: Examples of late-stage C–H methylation of bioactive molecules. ^aDAST activation. ^bFor insoluble sub...

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Scheme 9: A) Mn-catalyzed late-stage C–H alkynylation of peptides. B) Intramolecular late-stage alkynylative ...

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Figure 7: Proposed reaction mechanism of Mn(I)-catalyzed C–H alkynylation.

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Scheme 10: Late-stage Mn-catalyzed C–H allylation of peptides and bioactive motifs.

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Scheme 11: Intramolecular C–H allylative cyclic peptide formation.

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Scheme 12: Late-stage C–H glycosylation of tryptophan analogues.

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Scheme 13: Late-stage C–H glycosylation of tryptophan-containing peptides.

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Scheme 14: Late-stage C–H alkenylation of tryptophan-containing peptides.

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Scheme 15: A) Late-stage C–H macrocyclization of tryptophan-containing peptides and B) traceless removal of py...

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Review

Published 26 Jul 2021

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