NaH-mediated direct C–H arylation in the presence of 1,10-phenanthroline

Nozawa‐Kumada, Kanako; Iwakawa, Yuki; Onuma, So; Shigeno, Masanori; Kondo, Yoshinori

doi:10.1039/d0cc00730g

Cited by 6 publications

(4 citation statements)

References 77 publications

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“…The number of charge transfer is likely related to the distinguished E bd and E int . Based on the geometries of M-based pyrrole compounds, the Na atom leans to bind H and likely forms the generally stable NaH. − …”

Section: Resultsmentioning

confidence: 99%

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Luo

Zhao

et al. 2023

Inorg. Chem.

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Host–guest structure assembly is significant in the recognition of molecules, and the fullerene-based host–guest structure is a convenient method to determine the structures of fullerenes of which recognition is with many difficulties in experiments. Here, with density functional theory calculations, we designed several crown-shaped pyrrole-based hosts tuned by doping metal atoms (Li, Na, and K) for the effective recognition of C60 with modest interaction between the host and guest. Binding energy calculations showed an enhanced interaction of the concave–convex host–guest system with the doped metal atoms, enabling the selective recognition of C60. The electrostatic interaction between the host and guest was studied by the natural bond order charge analysis, reduced density gradient, and electrostatic potential. Furthermore, the UV–vis–NIR spectra of host–guest structures were simulated to give guidance on the release of the fullerene guest. With much expectation, this work would give a new strategy to design new hosts for effectively recognizing much more fullerene molecules with modest interaction and would be useful for the assembly involving fullerenes.

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Section: Resultsmentioning

confidence: 99%

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Luo

Zhao

et al. 2023

Inorg. Chem.

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“…Arylation of haloarenes with unactivated heteroarenes under transition-metal-free conditions was reported in the presence of NaH and 1,10-phenanthroline by Nozawa-Kumada, Kondo, and co-workers (Scheme 29). 38 Crosscoupling reactions of various substituted haloarenes and nonactivated heteroarenes were easily performed with this arylation methodology. Mechanistic studies have shown a phenyl radical intermediate is formed through SET from the radical species generated by the reaction of NaH and 1,10phenanthroline.…”

Section: Arylation Of Heteroarenes With Pseudohalides or Aryl Halidesmentioning

confidence: 99%

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

Uçar¹,

Daştan²

2021

Synthesis

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Transition-metal-free arylation reactions have attracted considerable attention, because of economic and environmental reasons over the past 40 years. In recent years, in particular, many efforts have been made to develop efficient transition-metal-free approaches for the arylation of heteroarenes. Covering the literature from 2015 to early 2021, this review aims to provide a comprehensive overview of the synthetic and mechanistic aspects of these atom economical and environmentally harmless reactions. 1 Introduction 2 Arylation of Pre-functionalized Heteroarenes 3 Direct C-H Arylation of Heteroarenes 3.1 C(Sp2)-H Arylation 3.2 C(sp3)-H Arylation 4 N-Arylation of Heteroarenes 5 Summary and Outlook

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“…[5] Recently, we reported the NaH-mediated coupling reaction of aryl halides with unactivated arenes in the presence of 1,10-phenanthroline. [6] This reaction proceeds via the addition of aryl radicals, formed through SET by NaH and 1,10-phenanthroline, to unactivated arenes (Scheme 1a). Regarding coupling reactions of aryl halides with alkenes, tert-butoxide salt-mediated Mizoroki-Heck type reactions with appropriate additives to afford stilbene derivatives have been reported (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

“…For reductants, the combination of strong bases and additives such as 1,10‐phenanthrolines, [4a,b] anilines, [4c,d] amines, [4e,f] and alcohols [4g,h] has attracted great attention over the past few decades, as electron donors can be easily generated in situ [5] . Recently, we reported the NaH‐mediated coupling reaction of aryl halides with unactivated arenes in the presence of 1,10‐phenanthroline [6] . This reaction proceeds via the addition of aryl radicals, formed through SET by NaH and 1,10‐phenanthroline, to unactivated arenes (Scheme 1a).…”

Section: Introductionmentioning

confidence: 99%

Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline

Nozawa‐Kumada

Onuma

Ono

et al. 2023

Chemistry A European J

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A transition‐metal‐free intermolecular coupling reaction of halocompounds with styrenes in the presence of NaH and 1,10‐phenanthroline was developed. This reaction afforded hydrocarbonated products with complete anti‐Markovnikov selectivity. The method allows the use of a wide range of halocompounds, including aryl and alkyl halides, and good functional group tolerance. Detailed mechanistic studies indicated that an anilide anion generated in situ by the NaH‐mediated reduction of 1,10‐phenanthroline works as an electron donor and a hydrogen source.

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NaH-mediated direct C–H arylation in the presence of 1,10-phenanthroline

Abstract: Transition-metal-free coupling of haloarenes with unactivated arenes has been developed in the presence of NaH and 1,10-phenanthroline.

Cited by 6 publications

References 77 publications

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes

Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline

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NaH-mediated direct C–H arylation in the presence of 1,10-phenanthroline

Abstract: Transition-metal-free coupling of haloarenes with unactivated arenes has been developed in the presence of NaH and 1,10-phenanthroline.

Cited by 6 publications

References 77 publications

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C60

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C60

Recent Advances in the Transition-Metal-Free Arylation of Hetero­arenes

Transition‐Metal‐Free Intermolecular Hydrocarbonation of Styrenes Mediated by NaH/1,10‐Phenanthroline

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Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Metal Atoms (Li, Na, and K) Tuning the Configuration of Pyrrole for the Selective Recognition of C₆₀

Recent Advances in the Transition-Metal-Free Arylation of Heteroarenes