ArticleAngewandte Chemie (International ed. in English)2020
Oxidative Addition of Water, Alcohols, and Amines in Palladium Catalysis.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 45 citations in OpenAlex.
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- A base-stabilized germavinylidene.Nature communications · 2025Article
- PdAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Palladium-Catalyzed Stitching of 1,3-C(spJournal of the American Chemical Society · 2023Article
- (CAAC)Pd(py) Catalysts Disproportionate to Pd(CAAC)Organometallics · 2023Article
- Recent Advances in the Domain of Cyclic (Alkyl)(Amino) Carbenes.Chemistry, an Asian journal · 2022Review
- Palladium Catalyst Recycling for Heck-Cassar-Sonogashira Cross-Coupling Reactions in Green Solvent/Base Blend.ChemSusChem · 2021Article
- Oxidative Addition of Water, Alcohols, and Amines in Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The homolytic cleavage of O-H and N-H or weak C-H bonds is a key elementary step in redox catalysis, but is thought to be unfeasible for palladium. In stark contrast, reported here is the room temperature and reversible oxidative addition of water, isopropanol, hexafluoroisopropanol, phenol, and aniline to a palladium(0) complex with a cyclic (alkyl)(amino)carbene (CAAC) and a labile pyridino ligand, as is also the case in popular N-heterocyclic carbene (NHC) palladium(II) precatalysts. The oxidative addition of protic solvents or adventitious water switches the chemoselectivity in catalysis with alkynes through activation of the terminal C-H bond. Most salient, the homolytic activation of alcohols and amines allows atom-efficient, additive-free cross-coupling and transfer hydrogenation under mild reaction conditions with usually unreactive, yet desirable reagents, including esters and bis(pinacolato)diboron.
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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.