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

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), all...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2015-08, Vol.13 (30), p.8298-8309
Main Authors: Reay, Alan J, Williams, Thomas J, Fairlamb, Ian J S
Format: Article
Language:English
Subjects:
Catalysis
Hydroxylation
Palladium - chemistry
Peptides - chemistry
Solvents - chemistry
Tryptophan - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01174d