Selective Approaches to α- and β-Arylated Vinyl Ethers.
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In this article, the authors developed simple and efficient protocols for palladium-catalyzed regioselective α-and β-arylations of structurally diverse vinyl ethers.Abstract:
We developed simple and efficient protocols for palladium-catalyzed regioselective α- and β-arylations of structurally diverse vinyl ethers. Both catalytic methods proceed under relatively mild reactions conditions applying to a broad substrate range including more complex compounds providing arylated glucal or isochromene. Lacking the common requirement of a large reagent excess, the transformations are highly economic and limiting the waste production. Results from computational studies (DFT) provided insight into the key factors determining the pronounced regioselectivities of the investigated reactions.read more
Citations
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Cooperative triple catalysis enables regioirregular formal Mizoroki–Heck reactions
TL;DR: In this paper , the authors describe an intermolecular α-arylation of electron-poor alkenes through cooperative nickel, photoredox and sulfinate catalysis, which operates under mild conditions and features excellent functional group tolerance.
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What the Heck?—Automated Regioselectivity Calculations of Palladium-Catalyzed Heck Reactions Using Quantum Chemistry
TL;DR: HeckQM as mentioned in this paper is a QM-based method that computes the relative energies of intermediates in Heck reaction that relate to the regioselective reaction outcome: branched (α), linear (β), or a mix of the two.
Journal ArticleDOI
1,1-Regioselective alkenylboration of styrenes enabled by palladium catalysis
TL;DR: In this article , a palladium-catalyzed, highly 1,1-regioselective alkenylboration of styrenes by using al-kenyl triflates and a diboron reagent as the coupling partners is reported.
Journal ArticleDOI
Assisted Tandem Pd Catalysis Enables Regiodivergent Heck Arylation of Transiently Generated Substituted Enol Ethers
Thomas Duhamel,Simone Scaringi,Baptiste Leforestier,Amalia I. Poblador-Bahamonde,Clément Mazet +4 more
TL;DR: In this article , two complementary Pd-catalyzed assisted tandem [isomerization/Heck arylation] reactions are reported, where the isomerization is conducted with a [Pd-H] precatalyst supported by tris-tert-butyl phosphine ligands.
References
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BookDOI
The Mizoroki–Heck Reaction
TL;DR: In this article, Jutand et al. describe the mechanism of the Mizoroki-Heck reaction and its application in organic synthesis, including the formation of Heterocycles.
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Palladacycles: Efficient New Catalysts for the Heck Vinylation of Aryl Halides
Wolfgang A. Herrmann,Christoph Brossmer,Claus-Peter Reisinger,Thomas Riermeier,Karl Öfele,Matthias Beller +5 more
TL;DR: Cyclopalladated complexes of the general formula [Pd2(μ-L)2(PC)2] (L = bridging ligand, e.g. OAc, Cl, Br, I; PC = cyclometallated P donor) are highly efficient catalysts for the Heck vinylation of aryl halides.
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Heck reaction catalyzed by PD-modified zeolites.
Laurent Djakovitch,Klaus Koehler +1 more
TL;DR: Heterogeneous catalysts prepared, characterized, and applied for the first time for catalytic carbon-carbon coupling reactions exhibit a high activity and selectivity toward the Heck reaction of aryl bromides with olefins for small palladium concentrations.
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Über Umlagerung von Phenol‐allyläthern in C‐Allyl‐phenole
TL;DR: Salmiak as mentioned in this paper verwandelter Verbindungen in 0-Alkylderivaten and C-Derivate umzulagern, tritt diese Neigung bei den 0 A 11 y lderivaten i n stitrkstem Mn5e hervor.
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Nonaqueous ionic liquids: superior reaction media for the catalytic Heck-vinylation of chloroarenes
TL;DR: The scope of the new reaction medium is outlined for the first time for the vinylation of various aryl halides using different mono- and disubstituted olefins as well as a variety of known palladium(0) and palladium (II) catalyst systems.