ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed.
- Article
- Wacker Oxidation of Trisubstituted Alkenes: Pd(II)-Catalyzed Oxidative Ring Expansion of Exocyclic α,β-Unsaturated Carbonyl to 2-Fluoro-1,3-Dicarbonyl Compounds.Angewandte Chemie (International ed. in English) · 2025Article
- Pd-Catalyzed Strain-Releasing Dyotropic Rearrangement: Ring-Expanding Amidofluorination of Methylenecyclobutanes.Journal of the American Chemical Society · 2025Article
- Competing Mechanisms in Palladium-Catalyzed Alkoxycarbonylation of Styrene.ACS catalysis · 2024Article
- Palladium/Iron-Catalyzed Wacker-Type Oxidation of Aliphatic Terminal and Internal Alkenes Using OACS omega · 2023Article
- Palladium-catalyzed intramolecular aza-Wacker-type cyclization of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles.RSC advances · 2023Article
- Wacker Oxidation of Methylenecyclobutanes: Scope and Selectivity in an Unusual Setting.Angewandte Chemie (International ed. in English) · 2023Article
- Sustainable Wacker-Type Oxidations.Angewandte Chemie (International ed. in English) · 2022Review
- PdAngewandte Chemie (International ed. in English) · 2022Article
- Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdAngewandte Chemie (International ed. in English) · 2022Article
- Intramolecular Aminolactonization for Synthesis of Furoindolin-2-One.Molecules (Basel, Switzerland) · 2021Article
- Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer.Angewandte Chemie (International ed. in English) · 2021Review
- Iron-Catalyzed Wacker-type Oxidation of Olefins at Room Temperature with 1,3-Diketones or Neocuproine as Ligands*.Angewandte Chemie (International ed. in English) · 2021Article
- Efficient Heterogeneous Palladium Catalysts in Oxidative Cascade Reactions.Accounts of chemical research · 2021Article
- Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.Journal of the American Chemical Society · 2021Article
- Controlling cyclization pathways in palladium(ii)-catalyzed intramolecular alkene hydro-functionalizationChemical science · 2020Article
- Salient features of theChemical science · 2020Review
- Concise Synthesis and Antimicrobial Evaluation of the Guanidinium Alkaloid Batzelladine D: Development of a Stereodivergent Strategy.Journal of the American Chemical Society · 2020Article
- Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.Israel journal of chemistry · 2020Article
- Programmable meroterpene synthesis.Nature communications · 2020Article
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2 authors.
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Abstract
In this review the stereochemistry of palladium-catalyzed addition of nucleophiles to alkenes is discussed, and examples of these reactions in organic synthesis are given. Most of the reactions discussed involve oxygen and nitrogen nucleophiles; the Wacker oxidation of ethylene has been reviewed in detail. An anti-hydroxypalladation in the Wacker oxidation has strong support from both experimental and computational studies. From the reviewed material it is clear that anti-addition of oxygen and nitrogen nucleophiles is strongly favored in intermolecular addition to olefin-palladium complexes even if the nucleophile is coordinated to the metal. On the other hand, syn-addition is common in the case of intramolecular oxy- and amidopalladation as a result of the initial coordination of the internal nucleophile to the metal.
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