ArticleJournal of the American Chemical Society2014
NiXantphos: a deprotonatable ligand for room-temperature palladium-catalyzed cross-couplings of aryl chlorides.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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33 citing papers in PubMed, 154 citations in OpenAlex.
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- Aryl acrylonitriles synthesis enabled by palladium-catalyzed α-alkenylation of arylacetonitriles with vinyl halides/triflates.Frontiers in chemistry · 2022Article
- Palladium-catalyzed benzylic C(spChemical science · 2021Article
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- Triarylmethanes and their Medium-Ring Analogues by Unactivated Truce-Smiles Rearrangement of Benzanilides.Angewandte Chemie (International ed. in English) · 2021Article
- Benzylic Methylene Functionalizations of Diarylmethanes.Chemistry, an Asian journal · 2020Review
- 10-Phenyl-10IUCrData · 2020Article
- Aryl Fluoride Activation Through Palladium-Magnesium Bimetallic Cooperation: A Mechanistic and Computational Study.ACS catalysis · 2020Article
- A denitrogenative palladium-catalyzed cascade for regioselective synthesis of fluorenes.Chemical science · 2019Article
- EnantioselectiveACS catalysis · 2018Article
- Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts.Journal of the American Chemical Society · 2018Article
- One-pot aminobenzylation of aldehydes with toluenes.Nature communications · 2018Article
- Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.Organic & biomolecular chemistry · 2018Article
- Palladium-Catalyzed Triarylation of spAdvanced synthesis & catalysis · 2018Article
- Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.Advanced synthesis & catalysis · 2017Article
- Palladium-catalysed synthesis of triaryl(heteroaryl)methanes.Nature communications · 2017Article
- Suzuki-Miyaura cross-coupling optimization enabled by automated feedback.Reaction chemistry & engineering · 2016Article
- Tandem C(spAdvanced synthesis & catalysis · 2016Article
- Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.Advanced synthesis & catalysis · 2016Article
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11 authors at 2 institutions in 1 country.
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Abstract
Although the past 15 years have witnessed the development of sterically bulky and electron-rich alkylphosphine ligands for palladium-catalyzed cross-couplings with aryl chlorides, examples of palladium catalysts based on either triarylphosphine or bidentate phosphine ligands for efficient room temperature cross-coupling reactions with unactivated aryl chlorides are rare. Herein we report a palladium catalyst based on NiXantphos, a deprotonatable chelating aryldiphosphine ligand, to oxidatively add unactivated aryl chlorides at room temperature. Surprisingly, comparison of an extensive array of ligands revealed that under the basic reaction conditions the resultant heterobimetallic Pd-NiXantphos catalyst system outperformed all the other mono- and bidentate ligands in a deprotonative cross-coupling process (DCCP) with aryl chlorides. The DCCP with aryl chlorides affords a variety of triarylmethane products, a class of compounds with various applications and interesting biological activity. Additionally, the DCCP exhibits remarkable chemoselectivity in the presence of aryl chloride substrates bearing heteroaryl groups and sensitive functional groups that are known to undergo 1,2-addition, aldol reaction, and O-, N-, enolate-α-, and C(sp(2))-H arylations. The advantages and importance of the Pd-NiXantphos catalyst system outlined herein make it a valuable contribution for applications in Pd-catalyzed arylation reactions with aryl chlorides.
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