ArticleACS catalysis2017
Mild and Regioselective Pd(OAc)
Article in ACS catalysis, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Arenediazonium-generated aryl radical and nitrile coupling cascade under neat and catalyst-free conditions: green synthesis of anilides.RSC advances · 2026Article
- Peptide modificationChemical science · 2026Article
- Palladium-Catalyzed C2 Functionalization of an Iodinated Tryptophan Scaffold for Fluorescent Probe Discovery.The Journal of organic chemistry · 2026Article
- Recent Advances in Bioconjugation of Aromatic Amino Acid Residues by a Reactivity-Guided Approach.Chemical record (New York, N.Y.) · 2026Review
- Revealing the Hidden Complexity and Reactivity of Palladacyclic Precatalysts: The P(ACS catalysis · 2024Article
- Photoredox C(2)-Arylation of Indole- and Tryptophan-Containing Biomolecules.Organic letters · 2024Article
- Overcoming Pd Catalyst Deactivation in the C-H Coupling of Tryptophan Residues in Water Using Air as the Oxidant.ACS catalysis · 2024Article
- Modular synthesis of clickable peptides via late-stage maleimidation on C(7)-H tryptophan.Nature communications · 2023Article
- Late-stage peptide labeling with near-infrared fluorogenic nitrobenzodiazoles by manganese-catalyzed C-H activation.Chemical science · 2023Article
- Computer vision for non-contact monitoring of catalyst degradation and product formation kinetics.Chemical science · 2023Article
- Temperature-induced formation of Pd nanoparticles in heterogeneous nanobiohybrids: application in C-H activation catalysis.Nanoscale advances · 2023Article
- Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.Organic process research & development · 2022Review
- Selective Labeling of Peptides with o-Carboranes via Manganese(I)-Catalyzed C-H Activation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- Electrooxidative dearomatization of biaryls: synthesis of tri- and difluoromethylated spiro[5.5]trienones.Chemical science · 2021Article
- C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)-Pd(ii) catalysisChemical science · 2021Article
- Late-Stage Diversification of Tryptophan-Derived Biomolecules.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Review
- Late-stage C(spChemical science · 2020Article
- Late-stage peptide C-H alkylation for bioorthogonal C-H activation featuring solid phase peptide synthesis.Nature communications · 2019Article
- Article
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Authors and funding
7 authors.
Funding
Abstract
A regioselective Pd-mediated C-H bond arylation methodology for tryptophans, utilizing stable aryldiazonium salts, affords C2-arylated tryptophan derivatives, in several cases quantitatively. The reactions proceed in air, without base, and at room temperature in EtOAc. The synthetic methodology has been evaluated and compared against other tryptophan derivative arylation methods using the CHEM21 green chemistry toolkit. The behavior of the Pd catalyst species has been probed in preliminary mechanistic studies, which indicate that the reaction is operating homogeneously, although Pd nanoparticles are formed during substrate turnover. The effects of these higher order Pd species on catalysis, under the reaction conditions examined, appear to be minimal: e.g., acting as a Pd reservoir in the latter stages of substrate turnover or as a moribund form (derived from catalyst deactivation). We have determined that TsOH shortens the induction period observed when [ArN
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Registered trials
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.