ArticleJournal of the American Chemical Society2015
Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 174 citations in OpenAlex.
- Enantioselective C-H functionalization: logic and applications in the total synthesis of natural products.Chemical science · 2026Review
- Nickel-catalyzed β-arylation and benzylation of 2'-hydroxychalcones to access warfarin analogues.Communications chemistry · 2025Article
- Total synthesis of (-)-cylindrocyclophane A facilitated by C-H functionalization.Science (New York, N.Y.) · 2024Article
- Remote-carbonyl-directed sequential Heck/isomerization/C(spNature communications · 2024Article
- Iron-Catalyzed Hydrobenzylation: Stereoselective Synthesis of (-)-Eugenial C.Journal of the American Chemical Society · 2023Article
- Sterically Controlled Late-Stage Functionalization of Bulky Phosphines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Directed Palladium-Catalyzed Acetoxylation of Indolines. Total Synthesis ofThe Journal of organic chemistry · 2022Article
- Regioselective C-H Functionalization of the Six-Membered Ring of the 6,5-Fused Heterocyclic Systems: An Overview.Molecules (Basel, Switzerland) · 2021Review
- Rhoda-Electrocatalyzed Bimetallic C-H Oxygenation by Weak O-Coordination.Angewandte Chemie (International ed. in English) · 2021Article
- Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.Chemical science · 2021Review
- Insights into Ruthenium(II/IV)-Catalyzed Distal C-H Oxygenation by Weak Coordination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Quadruple C-H activation coupled to hydrofunctionalization and C-H silylation/borylation enabled by weakly coordinated palladium catalyst.Nature communications · 2020Article
- Distal γ-C(spAngewandte Chemie (International ed. in English) · 2020Article
- Silanol: a bifunctional group for peptide synthesis and late-stage functionalization.Chemical science · 2020Article
- From Pd(OAc)Accounts of chemical research · 2020Article
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- Geminal group-directed olefinic C-H functionalization via four- to eight-membered exo-metallocycles.Nature communications · 2019Article
- Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis.ACS catalysis · 2019Article
- An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl.Molecules (Basel, Switzerland) · 2019Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Ortho-C(sp(2))-H olefination and acetoxylation of broadly useful synthetic building blocks phenylacetyl Weinreb amides, esters, and ketones are developed without installing an additional directing group. The interplay between the distal weak coordination and the ligand-acceleration is crucial for these reactions to proceed under mild conditions. The tolerance of longer distance between the target C-H bonds and the directing functional groups also allows for the functionalizations of more distal C-H bonds in hydrocinnamoyl ketones, Weinreb amides, and biphenyl Weinreb amides. Mechanistically, the coordination of these carbonyl groups and the bisdentate amino acid ligand with Pd(II) centers provides further evidence for our early hypothesis that the carbonyl groups of the potassium carboxylate are responsible for the directed C-H activation of carboxylic acids.
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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.