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Issue 30, 2015
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Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

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Abstract

Pd-mediated C–H bond functionalisation protocols have been designed and developed on tryptophan derivatives and tryptophan-containing peptides. The examination of different arylation reactions (three sets of different conditions A–C), all of which are notable for their low temperatures (≤40 °C), allowed identification of unified and complementary synthetic approaches toward a series of functionalised tryptophan-containing products. Tryptophan-containing peptides demonstrated to be susceptible to aromatic oxidation were successfully and selectively modified through the application of diaryliodonium salts in good yields.

Graphical abstract: Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

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The article was received on 10 Jun 2015, accepted on 26 Jun 2015 and first published on 06 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01174D
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Org. Biomol. Chem., 2015,13, 8298-8309

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    Unified mild reaction conditions for C2-selective Pd-catalysed tryptophan arylation, including tryptophan-containing peptides

    A. J. Reay, T. J. Williams and I. J. S. Fairlamb, Org. Biomol. Chem., 2015, 13, 8298
    DOI: 10.1039/C5OB01174D

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