Catalytic Carbon–Nitrogen Bond-Forming Cross-Coupling Using <i>N</i>-Trimethylsilylamines

Minami, Yasunori; Komiyama, Takeshi; Shimizu, Kenta; Hiyama, Tamejiro; Goto, Osamu; Ikehira, Hideyuki

doi:10.1246/bcsj.20150179

Cited by 7 publications

(5 citation statements)

References 64 publications

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“…Other examples of Buchwald–Hartwig indole N -arylation include the use of the ligands F4-1 [ 81 ], F4-2 [ 82 ], and t BuXphos ( F4-3 ) [ 83 ] ( Figure 4 ). In addition, the palladium-catalyzed amination of triflates [ 84 , 85 ]; cross-coupling reactions of silylated indoles with aryl halides [ 86 , 87 ]; and reactions that are catalyzed by Pd/ZnO nanoparticles [ 88 ], palladium immobilized on graphene [ 89 ], or silica-starch substrates [ 90 ] were used to prepare N -arylindoles. However, these procedures have mainly been developed for the N -arylation of amines, whereas the N -arylation of indoles was given for only a limited number of indole derivatives.…”

Section: Transition-metal-catalyzed N -Arylation Of Indolesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.

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Section: Transition-metal-catalyzed N -Arylation Of Indolesmentioning

confidence: 99%

Recent Progress Concerning the N-Arylation of Indoles

et al. 2021

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“…Holmes reported that N -TMS-amine coupled with aryl bromides in the presence of palladium acetate, JohnPhos, and a stoichiometric amount of Cs 2 CO 3 in supercritical CO 2 (eq ). Very recently, we disclosed that the C–N bond-forming cross-coupling between aryl bromides or chlorides and N -TMS-amines including N -TMS-aniline proceeded smoothly under Pd(dba) 2 /XPhos catalysts and CsF in N,N -dimethylimidazolidinone (DMI) . In the amination with N -TMS-amines, unsubstituted N–H bonds remain intact.…”

Section: C–n C–o and C–s Cross-coupling Reactionmentioning

confidence: 99%

Recent Advances in Transition-Metal-Catalyzed Synthetic Transformations of Organosilicon Reagents

2016

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Organosilicon compounds act as a nucleophile upon activation by an appropriate base and behave in a manner similar to main-group organometallic reagents. In the last decades, structurally divergent organosilicon reagents are available and have become more employed for synthetic transformation with the aid of transition-metal complexes, because organosilicon compounds are in general superior to other organometallic compounds in view of stability, solubility, nontoxicity, and easy-handling. Particularly, cross-coupling of organosilicon reagents with organic halides or pseudohalides has been considered to be a useful tool for constructing the carbon frameworks of various target molecules such as pharmaceuticals and π-conjugated functional materials. Perfluoroalkylsilicon compounds such as CF3SiEt3 have found use as reagents for the metal-catalyzed introduction of perfluoroalkyl groups into many substrates. In addition, functionalized organosilicon reagents are readily accessible by catalytic approach starting with appropriate hydrocarbons such as alkenes, alkynes, alkanes, and arenes. This article reviews recent advances in transition-metal-catalyzed transformations of organosilicon reagents according to the type of synthetic transformation and metal catalyst.

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“…TBP-TPA has been previously reported in the literature, in the context of nanoporous organic frameworks for CO 2 storage, [25] and MBP-TPA as photo and electroluminescent materials or as candidate for mechanistic investigations. [26][27][28][29][30][31][32] To the best of our knowledge, both MBP-TPA and TBP-TPA have never been used as PIs. The high molecular weight of TBP-TPA and its trifunctional character can also be very interesting for its potential migration stability.…”

Section: In This Study a New Generation Of Photoinitiator (Pi) Basedmentioning

confidence: 99%

Novel Photoinitiators Based on Benzophenone‐Triphenylamine Hybrid Structure for LED Photopolymerization

Liu

Brunel

Sun

et al. 2020

Macromol. Rapid Commun.

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In this study, a new generation of photoinitiator (PI) based on hybrid structures combining benzophenone and triphenylamine is proposed. Remarkably, these photoinitiators (noted monofunctional benzophenone‐triphenylamine (MBP‐TPA) and trifunctional benzophenone‐triphenylamine (TBP‐TPA)) are designed and developed for the photopolymerization under light‐emitting diodes (LEDs). Benzoyl substituents connected with triphenylamine moiety contribute to the excellent absorption properties which results in both high final conversions and polymerization rates in free radical photopolymerization (FRP). Remarkably, TBP‐TPA owning trifunctional benzophenone group exhibits a better Type II PI behavior than well‐known 2‐isopropylthioxanthone for photopolymerization under LED@365 and 405 nm irradiation. FRP and cationic photopolymerization of TBP‐TPA‐based systems are applied on 3D printing experiments, and good profiles of the 3D patterns are observed. The high molecular weight of TBP‐TPA associated with it trifunctional character can also be very interesting for a better migration stability of PIs that is a huge challenge. The development of this new generation of photoinitiators based on benzophenone hybrid structures is a real breakthrough. It reveals that the novel versatile photoinitiators based on benzophenone‐triphenylamine hybrid structures have great potentials for future industrial applications (e.g., 3D printing, composites, etc.).

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Catalytic Carbon–Nitrogen Bond-Forming Cross-Coupling Using N-Trimethylsilylamines

Cited by 7 publications

References 64 publications

Recent Progress Concerning the N-Arylation of Indoles

Recent Progress Concerning the N-Arylation of Indoles

Recent Advances in Transition-Metal-Catalyzed Synthetic Transformations of Organosilicon Reagents

Novel Photoinitiators Based on Benzophenone‐Triphenylamine Hybrid Structure for LED Photopolymerization

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