Journal ArticleDOI
Copper-Catalyzed Aerobic Oxidative C ? H Functionalizations: Trends and Mechanistic Insights
TLDR
This work has reported several recently reported Cu-catalyzed C-H oxidation reactions that feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II), and evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism.Abstract:
The selective oxidation of C-H bonds and the use of O(2) as a stoichiometric oxidant represent two prominent challenges in organic chemistry. Copper(II) is a versatile oxidant, capable of promoting a wide range of oxidative coupling reactions initiated by single-electron transfer (SET) from electron-rich organic molecules. Many of these reactions can be rendered catalytic in Cu by employing molecular oxygen as a stoichiometric oxidant to regenerate the active copper(II) catalyst. Meanwhile, numerous other recently reported Cu-catalyzed C-H oxidation reactions feature substrates that are electron-deficient or appear unlikely to undergo single-electron transfer to copper(II). In some of these cases, evidence has been obtained for the involvement of organocopper(III) intermediates in the reaction mechanism. Organometallic C-H oxidation reactions of this type represent important new opportunities for the field of Cu-catalyzed aerobic oxidations.read more
Citations
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Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
Journal ArticleDOI
Catalytic Functionalization of C(sp2) ? H and C(sp3) ? H Bonds by Using Bidentate Directing Groups
Guy Rouquet,Naoto Chatani +1 more
TL;DR: It would, therefore, appear that direct functionalization of substrates by activation of C-H bonds would eliminate the multiple steps and limitations associated with the preparation of functionalized starting materials.
Journal ArticleDOI
Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications
TL;DR: This Review comprehensively highlights recent advances in intra- and intermolecular C-H amination reactions utilizing late transition metal-based catalysts using mechanistic scaffolds and types of reactions.
Journal ArticleDOI
3d Transition Metals for C-H Activation.
Parthasarathy Gandeepan,Thomas Müller,Daniel Zell,Gianpiero Cera,Svenja Warratz,Lutz Ackermann +5 more
TL;DR: A comprehensive overview on first row transition metal catalysts for C-H activation until summer 2018 is provided.
Journal ArticleDOI
Mild metal-catalyzed C–H activation: examples and concepts
TL;DR: This review presents the current state of the art in this field and detail C-H activation transformations reported since 2011 that proceed either at or below ambient temperature, in the absence of strongly acidic or basic additives or without strong oxidants.
References
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Journal ArticleDOI
Organocopper(II) Complex of 21-Diphenylphosphoryl-Carbaporpholactone Hybrid: A Side-On Coordination Mode of Copper(II)
TL;DR: The diphenylphosphoryl-carbaporpholactone hybrid is a new aromatic porphyrinoid, which preserves the essential features of the carbaporphlactone frame and provides a suitable environment allowing stabilization of the organocopper(II) complex affording a peculiar side-on coordination of copper(II).
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Intramolecular oxidative phenol coupling. A new method
Journal ArticleDOI
Gas-Phase Study on the C-C Coupling of Naphthol Catalyzed by CUII·TMEDA : Evidence for the Key Role of Binuclear Clusters
Jana Roithová,Detlef Schröder +1 more
TL;DR: A pronounced counterion effect is found that correlates well with condensed-phase data: weakly bridging counterions yield less stable dicopper clusters and the coupling reaction hardly occurs, whereas better bridgingcounterions provide more stable clusters that make the coupling Reaction more efficient.
Journal ArticleDOI
Serendipity strikes again—efficient preparation of lithium tetramethylcuprate(III) via rapid injection NMR
Erika R. Bartholomew,Steven H. Bertz,Stephen K. Cope,Michael D. Murphy,Craig A. Ogle,Andy A. Thomas +5 more
TL;DR: Lithium tetramethylcuprate(III), Me(4)CuLi, the Cu(III) analog of the Gilman reagent, has been prepared in high yield from halo-Gilman reagents Me(2)Cu Li and found to have surprising thermal stability.
Journal ArticleDOI
Choice of Manganese(III) Complexes for the Synthesis of 4,4'-Biphenyldiols and 4,4'-Diphenoquiones.
TL;DR: In this paper, 2,6-disubstituted phenols are oxidized with tris(2,4-pentanedionato)manganese(III), [Mn(acac)3] in glacial acetic acid to give the corresponding 4,4′-biphenyldiols in high yields, whereas similar reactions using manganese( III) acetate, [Mmn(OAc)3], insted of [mn[Mn[acac]3] quantitatively yield the corresponding four
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