Metal-Free C–H Cross-Coupling toward Oxygenated Naphthalene-Benzene Linked Biaryls

Dohi, Toshifumi; Ito, Minoru; Itani, Itsuki; Yamaoka, Nobutaka; Morimoto, Koji; Fujioka, Hiromichi; Kita, Yasuyuki

doi:10.1021/ol202632h

Cited by 87 publications

(29 citation statements)

References 61 publications

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“…1,4‐Dimethoxynaphthalene and 3,5‐dimethoxytoluene can be cross‐coupled using various PIFA analogues 127. The best yield was obtained when FPIFA was used as the oxidant.…”

Section: Oxidative Aromatic Couplingmentioning

confidence: 99%

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

et al. 2013

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Does the dehydrogenative coupling of aromatic compounds mediated by AlCl3 at high temperatures and also by FeCl3, MoCl5, PIFA, or K3[Fe(CN)6] at room temperature proceed by the same mechanism in all cases? With the growing importance of the synthesis of aromatic compounds by double C-H activation to give various biaryl structures, this question becomes pressing. Since some of these reactions proceed only in the presence of non-oxidizing Lewis acids and some only in the presence of certain oxidants, the authors venture the hypothesis that, depending on the electronic structure of the substrates and the nature of the "catalyst", two different mechanisms can operate. One involves the intermediacy of a radical cation and the other the formation of a sigma complex between the acid and the substrate. The goal of this Review is to encourage further mechanistic studies hopefully leading to an in-depth understanding of this phenomenon.

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“…1,4‐Dimethoxynaphthalene and 3,5‐dimethoxytoluene can be cross‐coupled using various PIFA analogues 127. The best yield was obtained when FPIFA was used as the oxidant.…”

Section: Oxidative Aromatic Couplingmentioning

confidence: 99%

Comparison of Oxidative Aromatic Coupling and the Scholl Reaction

et al. 2013

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“…Subsequently, they have also reported the intermolecular C-H cross coupling of aromatic ethers 179 and 180 or 168 [58]. The key point of the reaction is the utilization of the perfluorinated PIFAs, which provided higher conversion and better selectivity compared with the traditional synthesis of biaryls using PIFA or PIDA.…”

Section: Cross-coupling Reactions Involving Hypervalent Iodinementioning

confidence: 99%

Double C–H Activation for the C–C bond Formation Reactions

Liu

Xiong

Chen

et al. 2018

COS

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Background: Among the numerous bond-forming patterns, C–C bond formation is one of the most useful tools for building molecules for the chemical industry as well as life sciences. Recently, one of the most challenging topics is the study of the direct coupling reactions via multiple C–H bond cleavage/activation processes. A number of excellent reviews on modern C–H direct functionalization have been reported by Bergman, Bercaw, Yu and others in recent years. Among the large number of available methodologies, Pdcatalyzed reactions and hypervalent iodine reagent mediated reactions represent the most popular metal and non-metal involved transformations. However, the comprehensive summary of the comparison of metal and non-metal mediated transformations is still not available. Objective: The review focuses on comparing these two types of reactions (Pd-catalyzed reactions and hypervalent iodine reagent mediated reactions) based on the ways of forming new C–C bonds, as well as the scope and limitations on the demonstration of their synthetic applications. Conclusion: Comparing the Pd-catalyzed strategies and hypervalent iodine reagent mediated methodologies for the direct C–C bond formation from activation of C-H bonds, we clearly noticed that both strategies are powerful tools for directly obtaining the corresponding pruducts. On one hand, the hypervalent iodine reagents mediated reactions are normally under mild conditions and give the molecular diversity without the presence of transition-metal, while the Pd-catalyzed approaches have a broader scope for the wide synthetic applications. On the other hand, unlike Pd-catalyzed C-C bond formation reactions, the study towards hypervalent iodine reagent mediated methodology mainly focused on the stoichiometric amount of hypervalent iodine reagent, while few catalytic reactions have been reported. Meanwhile, hypervalent iodine strategy has been proved to be more efficient in intramolecular medium-ring construction, while there are less successful examples on C(sp3)–C(sp3) bond formation. In summary, we have demonstrated a number of selected approaches for the formation of a new C–C bond under the utilization of Pd-catalyzed reaction conditions or hyperiodine reagents. The direct activations of sp2 or sp3 hybridized C–H bonds are believed to be important strategies for the future molecular design as well as useful chemical entity synthesis.

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“…44 Similarly, treatment of substituted naphthalene and phenyl ethers with the title compound, in addition to activation by BF 3 ·Et 2 O, afforded the naphthalene-benzene biaryl product in moderate yield in a regioselective fashion (eq 33). 45 The title compound was also effective in promoting intermolecular oxidative coupling processes between indoles and phenyl ethers under mild conditions (eq 34). 46 Notably, the PIFA-mediated CDC reactions have been used as key steps in the syntheses of more complex molecules, such as triphenylenes, Zn(II) or Ni(II) porphyrins, polyarenes, and bodipy dimers.…”

Section: Pifamentioning

confidence: 99%