Journal Article10.1038/NPROT.2007.364
Cu-catalyzed Goldberg and Ullmann reactions of aryl halides using chelating N- and O-based ligands
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TL;DR: The general procedure described in this text includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (gas chromatography and thin layer chromatography) and a procedure for the isolation, purification and characterization of the anticipated product.
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Abstract: The following protocol can be applied in the selective cross-coupling reaction of an amine with an aryl iodide or bromide using a copper (Cu)-based catalyst to provide the corresponding N-aryl amine. The general procedure described in this text includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (gas chromatography and thin layer chromatography) and a procedure for the isolation, purification and characterization of the anticipated product. Manipulation of the reagents can be done in the air, without the use of a glovebox; however, the cross-coupling reactions must be performed in a sealed reactor under an inert atmosphere. Three C-N bond-forming reactions are included in the protocol as representative examples of this procedure. Although the reactions can proceed in <1 h, the protocols, including workup, generally take 6-30 h to complete.
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Citations
Novel MOF‐Derived Co@N‐C Bifunctional Catalysts for Highly Efficient Zn–Air Batteries and Water Splitting
TL;DR: The rational design and synthesis of a new class of Co@N-C materials (C-MOF-C2-T) from a pair of enantiotopic chiral 3D MOFs by pyrolysis at temperature T is reported, exhibiting higher electrocatalytic activities for oxygen reduction and oxygen evolution reactions than that of commercial Pt/C and RuO2.
857
Cross-Coupling of Heteroatomic Electrophiles
TL;DR: The chemistry reviewed within provides perspective on the use of heteroatomic electrophiles, specifically silicon-, nitrogen-, boron-, oxygen-, and phosphorus-based electrophile in transition-metal catalyzed cross-coupling.
Remote C–H bond functionalization reveals the distance-dependent isotope effect
TL;DR: In this paper, both isotope and electronic effects observed in remote aryl C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladations is slower than the C−H bond cleavage, and they imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C −H bond increases.
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Photoinduced copper-catalyzed enantioselective coupling reactions.
TL;DR: A review of photo-induced copper-catalyzed enantioselective coupling reactions can be found in this paper , where the authors discuss the mechanistic aspects of these reactions.
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Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions
Younis Baqi,Christa E. Müller +1 more
TL;DR: This protocol describes the efficient, generally applicable Ullmann coupling reaction of bromaminic acid with alkyl- or aryl-amines in phosphate buffer under microwave irradiation using elemental copper as a catalyst, which leads to a number of biologically active compounds.
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References
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Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation
Steven V. Ley,Andrew Thomas +1 more
TL;DR: In this article, the authors highlight the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids as reaction partners in both O- and N-arylation.
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Copper in cross-coupling reactions: The post-Ullmann chemistry
TL;DR: A number of methods using various copper complexes and salts to carry out cross-coupling reactions leading to the formation of C heteroatom (C N, C O, C S, C P, C Se), C C, and C metal bonds have been proposed as discussed by the authors.
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