Catalytic hydrodebromination of aryl bromides by cobalt tetra-butyl porphyrin complexes with EtOH

Chen, Chen; Zuo, Huiping; Chan, Kin Shing

doi:10.1016/j.tet.2018.12.010

Cited by 10 publications

(3 citation statements)

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“…The authors also reported the occurrence of side-reactions for the MCR under study, such as aryl homocoupling and nucleophilic addition of the organometallic to the aromatic aldehyde (Scheme 3). However, although cobaltpromoted dehydrohalogenation has been previously reported in literature [36], its occurrence as side reaction in this MCR has not been previously considered. This byproduct may have been overlooked due to the fact that the dehydrohalogenation products derived from non-charge tagged compounds might have been removed during the isolation process of the γ-lactones (e.g., benzene derived from bromobenzene can be lost during sample concentration in a rotary evaporator).…”

Section: Mcr Online Monitoring Using Psi-esi-msmentioning

confidence: 78%

Real-time monitoring of a cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction

Crotti

Previdi

Donate

et al. 2020

Inorganica Chimica Acta

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Section: Mcr Online Monitoring Using Psi-esi-msmentioning

confidence: 78%

Real-time monitoring of a cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction

Crotti

Previdi

Donate

et al. 2020

Inorganica Chimica Acta

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“…The authors also reported the occurrence of side-reactions for the MCR under study, such as aryl homocoupling and nucleophilic addition of the organometallic to the aromatic aldehyde (Scheme 3). However, although cobalt-promoted dehydrohalogenation has been previously reported in literature [36], its occurrence as side reaction in this MCR has not been previously considered. This byproduct may have been overlooked due to the fact that the dehydrohalogenation products derived from non-charge tagged compounds might have been removed during the isolation process of the γ-lactones (e.g., benzene derived from bromobenzene can be lost during sample concentration in a rotary evaporator).…”

Section: Mcr Online Monitoring Using Psi-esi-msmentioning

confidence: 80%

Real-Time Monitoring of a Cobalt-Mediated One-Pot Transition Metal Catalyzed Multicomponent Reaction

Crotti¹,

Previdi²,

Donate³

et al. 2020

Preprint

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In this paper, pressurized sample infusion electrospray ionization mass spectrometry (PSI-ESI-MS) and FTIR spectroscopy was used to investigate the mechanism of a like-Barbier cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction (MCR). The use of charge-tagged aryl halides allowed for the detection of cobalt(II)-promoted hydrodehalogenation products. Although these products were also detected in the off-line ESI-MS monitoring, the ability of PSI-ESI-MS to track real-time changes in the reaction mixture composition proved cobalt(II) was responsible for the undesired transformation. The occurrence of cobalt(II)-promoted hydrodehalogenation as a side reaction in this MCR had not been considered in previous mechanistic proposals and represents an important mechanistic consideration.

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“…And sugars can be obtained from cellulose‐containing agricultural by‐products, including corncobs, straw, and sawdust. Despite the advantages, catalytic transfer hydrogenation of halides to corresponding dehalogenated compounds employing EtOH as a hydrogen source has been rarely established [10c,13] …”

Section: Introductionmentioning

confidence: 99%

Manganese‐Catalyzed Transfer Hydrodebromination of Aryl Bromides with Ethanol

et al. 2023

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A convenient PNP pincer manganese catalyzed transfer hydrogenation of bromides to corresponding debrominated aryl compounds using ethanol as the hydrogen sources is reported. Importantly, the application of biomass-derived ethanol highlights the sustainability of the methodology. The use of 6phenyl substituted triazine-based P ipr N 5 P ipr manganese pincer catalyst allows for the debromination of various aryl bromides with good yields. Notably, the process also occurs with bromides derived from several classes of natural products and bioactive compounds, such as citronellol, diacetone fructose, cholesterol, and vitamin E.

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Catalytic hydrodebromination of aryl bromides by cobalt tetra-butyl porphyrin complexes with EtOH

Cited by 10 publications

References 50 publications

Real-time monitoring of a cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction

Real-time monitoring of a cobalt-mediated one-pot transition metal-catalyzed multicomponent reaction

Real-Time Monitoring of a Cobalt-Mediated One-Pot Transition Metal Catalyzed Multicomponent Reaction

Manganese‐Catalyzed Transfer Hydrodebromination of Aryl Bromides with Ethanol

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