ArticleJournal of the American Chemical Society2011
A general method for copper-catalyzed arene cross-dimerization.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- C-H Activation of Pyridines by Boryl Pincer Complexes: Elucidation of Boryl-Directed C-H Oxidative Addition to Ir and Discovery of Transition Metal-Assisted Reductive Elimination from Boron at Rh.Journal of the American Chemical Society · 2024Article
- Molecular Sculpting: A Multipurpose Tool for Expedited Access to Various Fluorinated Arenes via Photocatalytic Hydrodefluorination of Benzoates.The Journal of organic chemistry · 2023Article
- Copper-Catalyzed Covalent Dimerization of Near-Infrared Fluorescent Cyanine Dyes: Synergistic Enhancement of Photoacoustic Signals for Molecular Imaging of Tumors.Analysis & sensing · 2022Article
- Cooperative C-H activation of pyridine by PBP complexes of Rh and Ir can lead to bridging 2-pyridyls with different connectivity to the B-M unit.Chemical science · 2021Article
- Silver Benzoate Facilitates the Copper-Catalyzed C-N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles.ACS omega · 2021Article
- Heterobiaryl synthesis by contractive C-C coupling via P(V) intermediates.Science (New York, N.Y.) · 2018Article
- Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center.Journal of the American Chemical Society · 2018Article
- Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.Journal of the American Chemical Society · 2017Article
- Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.Tetrahedron · 2015Article
- Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(spChemical science · 2015Article
- Modification of purine and pyrimidine nucleosides by direct C-H bond activation.Molecules (Basel, Switzerland) · 2015Review
- Cobalt-promoted dimerization of aminoquinoline benzamides.Organic letters · 2015Article
- C-H bond halogenation catalyzed or mediated by copper: an overview.Beilstein journal of organic chemistry · 2015Review
- Copper-promoted sulfenylation of sp2 C-H bonds.Journal of the American Chemical Society · 2012Article
- Copper-catalyzed CuAAC/intramolecular C-H arylation sequence: Synthesis of annulated 1,2,3-triazoles.Beilstein journal of organic chemistry · 2012Article
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2 authors.
Funding
Abstract
A general method for a highly regioselective copper-catalyzed cross-coupling of two aromatic compounds using iodine as an oxidant has been developed. The reactions involve an initial iodination of one arene followed by arylation of the most acidic C-H bond of the other coupling component. Cross-coupling of electron-rich arenes, electron-poor arenes, and five- and six-membered heterocycles is possible in many combinations. Typically, a 1/1.5 to 1/3 ratio of coupling components is used, in contrast to existing methodology that often employs a large excess of one of the arenes. Common functionalities such as ester, ketone, aldehyde, ether, nitrile, nitro, and amine are well-tolerated.
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