Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as  Terminal Oxidant

Obora, Yasushi; Ishii, Yasutaka

doi:10.3390/catal3040794

Cited by 26 publications

(15 citation statements)

References 71 publications

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“…Within this methodology, Pd-catalyzed intramolecular azaWacker-type oxidative reactions represent one crucial route to produce a range of 5-membered Ncontaining heterocycles [46][47][48][49][50][51]. However, intermolecular aza-Wacker-type oxidative amination has been rarely reported and protection of the amine nitrogen is often required in the reaction because palladium species would be deactivated via coordination of the unprotected amine to the metal center in most cases [41,[52][53][54]. Furthermore, benzoquinone, Cu(OAc)2 and other inorganic salt have often been used in Wacker oxidative reactions as oxidative reagents [55][56][57].…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the transition-metal-catalyzed sp 2 C-H amination reaction is one of the most demanding procedures to form C-N bonds [36,37]. In recent years, various late transition metal catalysts such as Pd [38][39][40][41], Ru [42], Rh [43], Ir [44], and Cu [45] have been applied in sp 2 C-H bond amination. Within this methodology, Pd-catalyzed intramolecular aza-Wacker-type oxidative reactions represent one crucial route to produce a range of 5-membered N-containing heterocycles [46][47][48][49][50][51].…”

Section: Introductionmentioning

confidence: 99%

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Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Mang

Yang

et al. 2016

Catalysts

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Abstract:The Pd(TFA) 2 -catalyzed [4+1] annulation of chained or cyclic α-alkenyl-dicarbonyl compounds and unprotected primary amines for "one-pot" synthesis of pyrroles is reported here. Enamination and amino-alkene were involved in this practical and efficient tandem reaction. The annulation products were isolated in moderate to excellent yields with O 2 as the terminal oxidant under mild conditions. In addition, this method was applied to synthesize highly regioselective aminomethylated and di(1H-pyrrol-3-yl)methane products.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Mang

Yang

et al. 2016

Catalysts

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“…Owing to the ubiquity of nitrogen-containing compounds in natural products, pharmaceuticals, agrochemicals, and synthetic intermediates, 1 the development of efficient methods for their synthesis has drawn considerable attention from chemists over recent decades. [2][3][4][5][6][7] Among the developed methods, direct C-H amination of simple starting materials is a more straightforward pathway 3 because of the atom economy in comparison with classical crosscoupling reactions such as the Buchwald-Hartwig amination. 4 In this field, many efforts have been devoted toward direct vinylic C-H aminations due to the prevalence of alkenes.…”

mentioning

confidence: 99%

“…4 In this field, many efforts have been devoted toward direct vinylic C-H aminations due to the prevalence of alkenes. [5][6][7] Conventionally, two types of reactions have been developed (Scheme 1). One is the aza-Wacker reaction in which a nucleophilic nitrogen source is utilized in the presence of external oxidants.…”

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confidence: 99%

Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide

Li¹,

Liao²,

Zhao³

2019

Synlett

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An efficient approach for the organoselenium-catalyzed aza-Wacker reaction of olefinic hydrazones and an oxime to form isoquinolinium imides and an isoquinoline N-oxide is developed. This transformation involves a direct intramolecular C–H amination using hydrazones and an oxime as imine-type nitrogen sources. This work not only provides a new approach for the construction of isoquinoline derivatives, but also expands the scope of nitrogen sources in electrophilic selenium catalysis.

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“…This synthetic strategy is now a powerful tool for efficient synthesis of multi-substituted arenes. Obora and Ishii summarize recent progress in palladium-catalyzed oxidative amination of alkenes with amines, using O2 as the terminal oxidant [6]. In this review, the uses of palladium catalysts combined with molybdovanadophosphate as a co-catalyst under O2 are presented.…”

mentioning

confidence: 99%

Palladium Catalysts for Cross-Coupling Reaction

Manabe

2015

Catalysts

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Palladium-catalyzed cross-coupling reactions constitute one of the most important and useful transformations in transition metal-catalyzed reactions [1][2][3]. Although this research field emerged in the 1970s, it is still attracting considerable attention in synthetic and organometallic chemistry. New catalysts and catalytic systems are being developed to further expand the utility of the reactions. This Special Issue on "Palladium Catalysts for Cross-Coupling Reaction" covers the diverse aspects of the ever-evolving field of palladium catalysts in cross coupling chemistry.This issue includes three reviews and three articles. The review by Ohashi and Ogoshi summarizes the recent development of palladium-catalyzed cross-coupling reactions of perfluoro organic compounds, such as tetrafluoroethylene and hexafluorobenzene [4]. One of the key steps of the reactions is the oxidative addition of a C-F bond to palladium(0). The finding that lithium iodide promotes the step, led the authors' to develop efficient cross-coupling with organozinc reagents. The reactions with boronates are also presented. The review by Manabe and Yamaguchi covers the Pd-catalyzed cross-coupling reactions in which the site-selectivities between the two halo groups of dihaloarene substrates were controlled by the catalysts used [5]. Some new ligands for palladium were designed to realize high selectivity. This synthetic strategy is now a powerful tool for efficient synthesis of multi-substituted arenes. Obora and Ishii summarize recent progress in palladium-catalyzed oxidative amination of alkenes with amines, using O2 as the terminal oxidant [6]. In this review, the uses of palladium catalysts combined with molybdovanadophosphate as a co-catalyst under O2 are presented. In addition, the interesting results of amination using O2 as the sole oxidant are also provided. In the article by Sajiki and Monguchi et al., a successful example of continuous flow Suzuki-Miyaura coupling reactions of haloarenes with arylboronic acids is described [7]. Only 20 s were required for the single-pass flow through a cartridge filled with palladium on carbon to afford the desired coupling products in high yields. Takanami et al. developed a synthetic method of pentafluorophenyl-and related polyfluorophenyl-substituted porphyrins [8]. By choosing the appropriate palladium catalyst OPEN ACCESS

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Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Cited by 26 publications

References 71 publications

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Practical Pd(TFA)2-Catalyzed Aerobic [4+1] Annulation for the Synthesis of Pyrroles via “One-Pot” Cascade Reactions

Organoselenium-Catalyzed Aza-Wacker Reactions: Efficient Access to Isoquinolinium Imides and an Isoquinoline N-Oxide

Palladium Catalysts for Cross-Coupling Reaction

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