Catalytic Functionalization of Arenes and Alkanes via C−H Bond Activation

Jia, Chengguo; Kitamura, Tsugio; Fujiwara, Yoshiyuki

doi:10.1021/ar000209h

Cited by 1,389 publications

(429 citation statements)

References 48 publications

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“…178 This because of the need to valorise natural gas and new fossil fuel resources, and especially alkanes. 179 In this context, the mild oxidation of methane to useful products like methanol or formaldehyde, rather than full combustion to CO 2 , has a very important role.…”

Section: Methane and Hydrocarbons Partial Oxidationmentioning

confidence: 99%

Catalytic oxygen activation versus autoxidation for industrial applications: a physicochemical approach

Liu

Ryabenkova

Conte

2015

Phys. Chem. Chem. Phys.

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The activation and use of oxygen for the oxidation and functionalization of organic substrates is among the most important reactions in a chemist's toolbox. Nevertheless, despite the vast literature on catalytic oxidation, the phenomenon of autoxidation, an ever-present background reaction that occurs in virtually every oxidation process, is often neglected. In contrast, autoxidation can affect the selectivity to a desired product, to those dictated by pure freeradical chain pathways, thus affecting the activity of any catalyst used to carry out a reaction.This critical review compares catalytic oxidation routes by transition metals versus autoxidation, particularly focusing on the industrial context, where highly selective and "green" processes are needed. Furthermore, the application of useful tests to discriminate between different oxygen activation routes, especially in the area of hydrocarbon oxidation, with the aim of an enhanced catalyst design, is described and discussed. In fact, one of the major targets of selective oxidation is the use of molecular oxygen as ultimate oxidant, combined with the development of catalysts capable to perform the catalytic cycle in a real energy and cost effective manner on a large scale. To achieve this goal, insights from metallo-proteins that could find application in some areas of industrial catalysis are presented, as well as considering the physicochemical principles that are at the fundament of oxidation and autoxidation processes.3

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Section: Methane and Hydrocarbons Partial Oxidationmentioning

confidence: 99%

Catalytic oxygen activation versus autoxidation for industrial applications: a physicochemical approach

Liu

Ryabenkova

Conte

2015

Phys. Chem. Chem. Phys.

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“…1,2 First discovered by Fujiwara and Moritani as a Pd-mediated process 3 and later developed into a Pd-catalyzed 4 coupling of benzene with styrene, this reaction has been reported with a range of arenes, 5−21 heteroarenes, 8,22−29 and alkenes. 30,31 These oxidative olefinations of aryl C−H bonds have the potential to provide, in a single step, access to vinylarenes for further functionalization during the synthesis of complex structures.…”

Section: ■ Introductionmentioning

confidence: 99%

Iridium-Catalyzed Oxidative Olefination of Furans with Unactivated Alkenes

2014

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The oxidative coupling of arenes and alkenes is an attractive strategy for the synthesis of vinylarenes, but reactions with unactivated alkenes have typically occurred in low yield. We report an Ir-catalyzed oxidative coupling of furans with unactivated olefins to generate branched vinylfuran products in high yields and with high selectivities with a second alkene as the hydrogen acceptor. Detailed mechanistic experiments revealed catalyst decomposition pathways that were alleviated by the judicious selection of reaction conditions and application of new ligands.

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“…For instance, controlled catalyst pretreatment was found to extend the catalyst lifetime to more than 100 turnovers. In the homogeneous reactions using various oxidants the turnover values vary between 3 and 280 with an average turnover of 83 [10,11]. Using a co-catalyst (HPMO 12 + HPMo 11 V 1 ) the highest TON under O 2 was 121 [15].…”

Section: Scheme 2 Oxidative Coupling Of Anisole With Ethyl Trans-cinmentioning

confidence: 99%

“…At the end of the catalytic cycle the active Pd(II) species are reduced to Pd(0), requiring continuous reoxidation for the reaction to proceed [11]. The convenient oxidants are Ag(I), Cu(II), peroxides, oxygen, or the air.…”

Section: Introductionmentioning

confidence: 99%

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Heterogeneous alkenylation of aromatics under oxygen

Hájek¹,

Dams²,

Detrembleur³

et al. 2007

Catalysis Communications

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A novel heterogeneous Pd/polymer catalyst containing co-catalytic functional groups catalyses the direct alkenylation of anisole with ethyl trans-cinnamate under oxygen. The properties of the polymeric catalyst were compared to other immobilised catalysts. The activity of the polymeric catalyst typically increased with temperature and oxygen pressure exhibiting the optimal activity up to 100 TON at 383 K under 1. 2 MPa of O 2 . The most abundant product was 3-(p-methoxyphenyl)-3-phenylpropanoate (≈45%). The reaction selectivity was practically independent of the conditions. Split-tests and AAS measurements confirm heterogeneous character of the catalyst.

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Catalytic Functionalization of Arenes and Alkanes via C−H Bond Activation

Cited by 1,389 publications

References 48 publications

Catalytic oxygen activation versus autoxidation for industrial applications: a physicochemical approach

Catalytic oxygen activation versus autoxidation for industrial applications: a physicochemical approach

Iridium-Catalyzed Oxidative Olefination of Furans with Unactivated Alkenes

Heterogeneous alkenylation of aromatics under oxygen

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