ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 25 citations in OpenAlex.
- Late-Stage Modification of Halotryptophan-Containing Peptides Via Negishi Cross-Coupling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Structural basis of regioselective double halogenation of the β-carboline tryptoline by the single-component halogenase AetF.Acta crystallographica. Section D, Structural biology · 2026Article
- Efficient and Rapid Arylation of NH₂-Unprotected Bromobisindole Ethanamines via Suzuki-Miyaura Coupling: Generating New Leads Against Leishmania.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Biosynthesis of Halogenated Tryptophans for Protein Engineering Using Genetic Code Expansion.Chembiochem : a European journal of chemical biology · 2024Article
- Halogenation of Peptides and Proteins Using Engineered Tryptophan Halogenase Enzymes.Biomolecules · 2022Article
- Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- Multifunctional Core-Shell Microgels as Pd-Nanoparticle Containing Nanoreactors With Enhanced Catalytic Turnover.Frontiers in chemistry · 2022Article
- Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021Review
- Suzuki-Miyaura Cross-Coupling of Bromotryptophan Derivatives at Ambient Temperature.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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7 authors at 1 institution in 1 country.
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Abstract
Mild reaction conditions are highly desirable for bio-orthogonal side chain derivatizations of amino acids, peptides or proteins due to the sensitivity of these substrates. Transition metal catalysed cross-couplings such as Suzuki-Miyaura reactions are highly versatile, but usually require unfavourable reaction conditions, in particular, when applied with aryl bromides. Ligand-free solvent-stabilised Pd-nanoparticles represent an efficient and sustainable alternative to conventional phosphine-based catalysts, because the cross-coupling can be performed at considerably lower temperature. We report on the application of such a highly reactive heterogeneous catalyst for the Suzuki-Miyaura cross-coupling of brominated tryptophan derivatives. The solvent-stabilised Pd-nanoparticles are even more efficient than the literature-known ADHP-Pd precatalyst. Interestingly, the latter also leads to the formation of quasi-homogeneous Pd-nanoparticles as the catalytic species. One advantage of our approach is the compatibility with aqueous and aerobic conditions at near-ambient temperatures and short reaction times of only 2 h. The influence of different N
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.