Search Results - "Freese, Tyll"
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Recent advances in neutral and anionic N-heterocyclic carbene – betaine interconversions. Synthesis, characterization, and applications
Published in ARKIVOC (07-08-2013)Get full text
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Cycloadditions of anionic N-heterocyclic carbenes of sydnone imines
Published in Tetrahedron letters (02-05-2019)“…[Display omitted] •Deprotonated sydnone imines can be represented as anionic N-heterocyclic carbenes.•Adduct formation to di-isopropylazodicarboxylate (DIAD)…”
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An Iterative Approach to Unsaturated and Partially Saturated [7]Helicenes
Published in Organic letters (18-02-2022)“…We report a simple, iterative strategy for the synthesis of [7]helicenes starting from substituted 1,4-xylene building blocks. In the first step, we take…”
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Functionalization of Sydnones with Donor‐Acceptor Cyclopropanes, Cyclobutanes, and Michael Acceptors
Published in European journal of organic chemistry (12-03-2021)“…We present a Lewis acid catalyzed nucleophilic ring‐opening of donor‐acceptor cyclopropanes and ‐butanes by sydnones, utilizing their respective 1,3‐ and…”
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One-Pot Strategy for Symmetrical and Unsymmetrical BOIMPY Fluorophores
Published in Journal of organic chemistry (05-02-2021)“…We report the improved direct access to red-emitting BOIMPY fluorophores (λ ≈ 600 nm) via a simple one-pot approach. Our method starts from easily available…”
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Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenes
Published in RSC advances (06-02-2019)“…The sydnone imines (5-benzoylimino)-3-(2-methoxyphenyl)-sydnone imine and molsidomine were deprotonated at C4 to give sydnone imine anions which can be…”
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Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold
Published in Tetrahedron (07-09-2017)“…The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4…”
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Borane adducts of punicine and of its dehydroxy derivatives (pyridinium-1-yl)-2- and 3-phenolates
Published in Tetrahedron (06-11-2020)“…The natural product punicine (Punica granatum) exists in two tautomeric forms, the cross-conjugated mesomeric betaine…”
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The intersection of allenylidenes and mesomeric betaines. 1-Methylpyridinium-2-acetylide and its palladium complexes
Published in Tetrahedron (08-12-2016)“…The anion of 2-ethynyl-1-methylpyridinium salts, which polymerized rapidly, can be represented as the mesomeric betaine 1-methylpyridinium-2-acetylide or as…”
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Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts
Published in ARKIVOC free online journal of organic chemistry (17-06-2020)Get full text
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Heterocycle Syntheses with Anionic N‐Heterocyclic Carbenes: Ring Transformations of Sydnone Imine Anions
Published in European journal of organic chemistry (17-04-2018)“…Sydnone imines were deprotonated at the C4 position to give lithium‐stabilized anions, which proved to be stable for several months in solution. These anions…”
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Anionic N-heterocyclic carbenes by decarboxylation of sydnone-4-carboxylates
Published in Tetrahedron (19-04-2018)“…Unstable N-heterocyclic carbenes can be masked and stabilized as pseudo-cross-conjugated hetarenium-carboxylates which decarboxylate on warming. This study…”
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Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines
Published in Journal of organic chemistry (20-05-2016)“…3-Ethynylquinoline was subjected to a Sonogashira–Hagihara reaction with methyl 2-, 3-, and 4-bromobenzoates, respectively, and then N-methylated to give…”
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Sulfur, mercury, and boron adducts of sydnone imine derived anionic N-heterocyclic carbenesElectronic supplementary information (ESI) available: Spectra, details of the X-ray analyses. CCDC 1889199 (27a), 1889200 (28a), 1889201 (29), 1889202 (30a) and 1889203 (31a) contain the supplementary crystallographic data for this paper. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9ra00294d
Published 06-02-2019“…The sydnone imines (5-benzoylimino)-3-(2-methoxyphenyl)-sydnone imine and molsidomine were deprotonated at C4 to give sydnone imine anions which can be…”
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Palladium complexes of anionic N-heterocyclic carbenes derived from sydnones in catalysis
Published in Zeitschrift für Naturforschung. B, A journal of chemical sciences (01-06-2016)“…The anion of -phenylsydnone, which can be generated on treatment of -phenylsydnone with cyanomethyllithium without decomposition, can be represented as…”
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