Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant

Foschi, Francesca; Loro, Camilla; Sala, Roberto; Oble, Julie; Presti, Leonardo Lo; Beccalli, Egle M.; Poli, Giovanni; Broggini, Gianluigi

doi:10.1021/acs.orglett.0c00010

Cited by 35 publications

(21 citation statements)

References 56 publications

(24 reference statements)

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“…Co-N-C 也可以通过电催化二电子 ORR 途径产生过氧化氢(H2O2). H2O2 是一种广泛用于工业和家庭的绿色氧化剂, 在废水处理 [16] 、杀菌急救、化学合成 [17,18] 、能量载体 [19,20] 等方面都有着广泛的应用. 目前工业上合成 H2O2 的方法主要为蒽醌法, 存在生产污染严重、副产物多、设备昂贵等问题.…”

Section: 剂(M-n-c)凭借其导电性强、原子利用率高、活unclassified

Recent progress in Co-N-C single-atom catalysts for the electrochemical oxygen reduction reaction

Wang¹,

Chen²,

Han³

et al. 2021

Sci. Sin.-Chim

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Cobalt-based single-atom catalyst supported on porous nitrogen-doped carbon (Co-N-C) has received extensive attention due to the excellent catalytic performance in the electrochemical oxygen reduction reaction (ORR). Co-N-C can catalyze ORR via different electron transfer pathways to generate water (H 2O) or hydrogen peroxide (H2O2), respectively. Therefore, the rational design of the active sites and the optimization of the catalytic conditions are the key factors in the development of metal-air batteries, fuel cells and chemical industry. However, the key factors determining the selectivity of the ORR are still undefined. This review reports the recent progress on Co-N-C single-atom catalysts for the electrochemical ORR. We will focus on the microenvironment of the singleatom sites and the test conditions for oxygen reduction reaction, with attention on the oxygen adsorption energy and reaction intermediate binding energy. Last, by highlighting the key factors for the selectivity determination, we wish to shed some light on the further development of Co-N-C for ORR.

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Section: 剂(M-n-c)凭借其导电性强、原子利用率高、活unclassified

Recent progress in Co-N-C single-atom catalysts for the electrochemical oxygen reduction reaction

Wang¹,

Chen²,

Han³

et al. 2021

Sci. Sin.-Chim

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“…Recently, an intramolecular palladium catalyzed aminoazidation of unactivated terminal alkenes in oxidative conditions was developed [96]. The reaction occurs in mild conditions in the presence of a Pd(II)-catalyst and H 2 O 2 as oxidant agent allowing to obtain five-, six-, and seven-membered heterocyclic rings through a selective exo-cyclization (Scheme 39).…”

Section: Amination/azidationmentioning

confidence: 99%

Transition Metal Catalyzed Azidation Reactions

et al. 2020

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A wide range of methodologies for the preparation of organic azides has been reported in the literature for many decades, due to their interest as building blocks for different transformations and their applications in biology as well as in materials science. More recently, with the spread of the use of transition metal-catalyzed reactions, new perspectives have also materialized in azidation processes, especially concerning the azidation of C–H bonds and direct difunctionalization of multiple carbon-carbon bonds. In this review, special emphasis will be placed on reactions involving substrates bearing a leaving group, hydroazidation reactions and azidation reactions that proceed with the formation of more than one bond. Further reactions for the preparation of allyl and vinyl azides as well as for azidations involving the opening of a ring complete the classification of the material.

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“…The introduction of the chloromethyl appendage should facilitate their post-functionalization towards more complex molecules. In 2020, the aminoazidation domino process was described for the synthesis of the 1,4benzodiazepines 71a-c starting from the unactivated N-allyl-anthranilamides 70a−c through a selective 7-exo-cyclization (Scheme 35) [93]. The reaction proceeded under mild conditions with NaN3 as the azide anion source and H2O2 as the inexpensive oxidant agent.…”

Section: Scheme 26mentioning

confidence: 99%

Palladium-Catalyzed Benzodiazepines Synthesis

2020

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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Intramolecular Aminoazidation of Unactivated Terminal Alkenes by Palladium-Catalyzed Reactions with Hydrogen Peroxide as the Oxidant

Cited by 35 publications

References 56 publications

Recent progress in Co-N-C single-atom catalysts for the electrochemical oxygen reduction reaction

Recent progress in Co-N-C single-atom catalysts for the electrochemical oxygen reduction reaction

Transition Metal Catalyzed Azidation Reactions

Palladium-Catalyzed Benzodiazepines Synthesis

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