Regioselective Acceptorless Dehydrogenative Coupling of N‐Heterocycles toward Functionalized Quinolines, Phenanthrolines, and Indoles

Talwar, Dinesh; González-de-Castro, Ángela; Li, Ho Yin; Xiao, Jianliang

doi:10.1002/anie.201500346

Cited by 87 publications

(25 citation statements)

References 66 publications

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“…Recently, the acceptorless dehydrogenation (AD) of primary amines to imines was shown to be an attractive method for their preparation as fewer side‐products are obtained under more inert conditions (with the release of H 2 ) . As this reaction is more thermodynamically challenging, the acceptorless dehydrogenation of primary amines has received less attention compared to that of N‐heterocycles, with the later reaction having been widely explored for hydrogen storage applications …”

Section: Introductionmentioning

confidence: 99%

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core–Shell Cobalt Nanoparticles

Cui

Junge

et al. 2020

Angew Chem Int Ed

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Core-shell nanocatalysts are attractive due to their versatility and stability.Here,wedescribe cobalt nanoparticles encapsulated within graphitic shells prepared via the pyrolysis of acationic poly-ionic liquid (PIL) with acobalt(II) chloride anion. The resulting material has ac ore-shell structure that displays excellent activity and selectivity in the self-dehydrogenation and hetero-dehydrogenation of primary amines to their corresponding imines.F urthermore,t he catalyst exhibits excellent activity in the synthesis of secondary imines from substrates with various reducible functional groups (C=C, CC and CN) and amino acid derivatives.

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Section: Introductionmentioning

confidence: 99%

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core–Shell Cobalt Nanoparticles

Cui

Junge

et al. 2020

Angew Chem Int Ed

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“…Our groupr ecently demonstratedt hat iridacycle catalysts could also enable both the hydrogen-borrowing reaction and dehydrogenative coupling of amines and alcohols. [7] Here, we present ab inuclear Rh complex-catalyzedc hemoselective alkylation ando lefination of alkylnitriles with alcohols,w ith the selectivity controlled by simply alteringt he reaction atmosphere (Scheme 1, bottom).T he alkylation reaction performed under Ar is ah ydrogen-borrowingr eaction, whereas the olefinationr eaction underO 2 is adehydrogenativec oupling process.…”

Section: In Memory Of Takao Ikariyamentioning

confidence: 99%

Atmosphere‐Controlled Chemoselectivity: Rhodium‐Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols

Liu

Tang

et al. 2017

Chemistry A European J

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The chemoselective alkylation and olefination of alkylnitriles with alcohols have been developed by simply controlling the reaction atmosphere. A binuclear rhodium complex catalyzes the alkylation reaction under argon through a hydrogen‐borrowing pathway and the olefination reaction under oxygen through aerobic dehydrogenation. Broad substrate scope is demonstrated, permitting the synthesis of some important organic building blocks. Mechanistic studies suggest that the alkylation product may be formed through conjugate reduction of an alkene intermediate by a rhodium hydride, whereas the formation of olefin product may be due to the oxidation of the rhodium hydride complex with molecular oxygen.

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“…These reactions generated in situ nucleophilic enamines that could react with various electrophiles. A further cascade process was developed by combining these dehydrogenative couplings with Friedel–Crafts additions …”

Section: Dehydrogenationmentioning

confidence: 99%

Pentamethylcyclopentadienyl Iridium(III) Metallacycles Applied to Homogeneous Catalysis for Fine Chemical Synthesis

et al. 2016

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Pentamethylcyclopentadienyl cyclometallated complexes have been used to catalyse a variety of organic transformations over the last decades. However, the huge potential of pentamethylcyclopentadienyl iridacycles has only been truly recognised in recent years. Indeed, an upsurge of reports on such new half‐sandwich iridium(III) metallacycles has been observed. The application of these organometallic complexes in various homogeneous catalysed organic reactions has led to the development of environmentally and economically beneficial routes towards important and highly functionalised fine chemicals. Studied reactions include hydrogenation, amine alkylation, dehydrogenation, oxidation and hydrofunctionalisation reactions as well as dynamic kinetic resolutions (DKR). This minireview focusses specifically on the recent applications of half‐sandwich iridium(III) metallacycles in such processes.

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Regioselective Acceptorless Dehydrogenative Coupling of N‐Heterocycles toward Functionalized Quinolines, Phenanthrolines, and Indoles

Cited by 87 publications

References 66 publications

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core–Shell Cobalt Nanoparticles

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core–Shell Cobalt Nanoparticles

Atmosphere‐Controlled Chemoselectivity: Rhodium‐Catalyzed Alkylation and Olefination of Alkylnitriles with Alcohols

Pentamethylcyclopentadienyl Iridium(III) Metallacycles Applied to Homogeneous Catalysis for Fine Chemical Synthesis

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