Oxanickelacyclopentene Derivatives from Nickel(0), Carbon Dioxide, and Alkynes

Burkhart, G.; Hoberg, Heinz

doi:10.1002/anie.198200762

Cited by 102 publications

(39 citation statements)

References 3 publications

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“…During the first half of the 1980s, Hoberg and co-workers were able -among others -to demonstrate various oxidative couplings between CO 2 and alkenes [36,37], dienes [38,39], alkynes [40][41][42], and allenes [43], leading to a deeper understanding of the elementary steps involved in these processes. For example, it was revealed that a very common pathway of CO 2 activation at Ni(0) metal centers proceeds via the formation of five-memberedring nickelalactones.…”

Section: Reactions With Group 10 Metalsmentioning

confidence: 99%

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Brill

Lazreg

Cazin

et al. 2015

Topics in Organometallic Chemistry

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The development of sustainable chemical processes is a long-standing challenge. Carbon dioxide represents a renewable C1 building block for organic synthesis and industrial applications as an alternative to other common feedstocks which are based on natural gas, petroleum oil, or coal. Apart from the advantages associated with the nontoxicity and abundance of CO 2 , its utilization further enables the reduction in its atmospheric content, which contributes significantly to the greenhouse effect. Although widespread application of CO 2 in organic synthesis -even on an industrial scale -will not be able to fully compensate for the steadily increasing atmospheric quantities produced (mainly by the combustion of fuels), ecological and economical factors make its usage highly desirable. Therefore, tremendous efforts toward activation and utilization of CO 2 have been made by the scientific community over the last 30 years, and, as a result, the number of highly efficient transition metal-catalyzed CO 2 -incorporative reactions has increased dramatically, especially within the last decade. The achievements in the development of sustainable and economic chemical processes for the carboxylation of organic molecules with CO 2 are presented in detail in this chapter.

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Section: Reactions With Group 10 Metalsmentioning

confidence: 99%

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Brill

Lazreg

Cazin

et al. 2015

Topics in Organometallic Chemistry

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“…Prompted by the seminal Ni-catalyzed oxidative cyclization work of Inoue for preparing 2-pyrones using CO 2 as coupling partner [30], Burkhart and Hoberg reported the isolation of an oxanickelacyclopentene (nickelalactone) from the coupling of 2-butyne and CO 2 with Ni(cdt) (cdt = 1,5,6-cyclododecatriene) and N,N,N',N'-tetramethylethylenediamine (TMEDA) [31]. The authors highlighted that the corresponding α,β-unsaturated carboxylic acid can be easily within reach upon simple protonolysis (Scheme 1).…”

Section: Stoichiometric Processesmentioning

confidence: 99%

“…The first metal-catalyzed carboxylation of alkynes with CO 2 was reported three years before the isolation of nickelalactones by Hoberg [31]. Specifically, in 1977 Inoue described the carboxylation of alkynes with CO 2 leading to the formation of 2-pyrones.…”

Section: Catalytic Carboxylation Of Alkynesmentioning

confidence: 99%

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Juliá‐Hernández¹,

Gaydou²,

Serrano³

et al. 2016

Topics in Current Chemistry Collections

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Abstract. The sustainable utilization of available feedstock materials for preparing valuable compounds holds great promise to revolutionize approaches in organic synthesis. In this regard, the implementation of abundant and inexpensive carbon dioxide (CO 2 ) as a C1 building block has recently attracted a considerable attention. Among the different alternatives in CO 2 fixation, the preparation of carboxylic acids, relevant motifs in pharmaceuticals and agrochemicals, is particularly appealing, thus providing a rapid and unconventional entry to building blocks that are typically prepared via wasteproducing protocols. While significant advances have been realized, the utilization of simple unsaturated hydrocarbons as coupling partners in carboxylation events is undoubtedly of utmost academic and industrial relevance, as two available feedstock materials can be combined in a catalytic fashion. This review article aims to describe the main achievements on the direct carboxylation of unsaturated hydrocarbons with CO 2 by using cheap and available Ni or Fe catalytic species.

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“…In the following years a lot of work was devoted to the oxidative coupling of CO 2 with olefins at nickel complexes [38] by many groups, with detailed fundamental knowledge resulting from the systematic work by Hoberg [62]. The nickelalactones undergo hydrolysis in the presence of mineral acids leading to the degradation of the nickel complex and formation of the free acrylic acid in a stoichiometric reaction.…”

Section: Oxidative Coupling Of Co 2 and Olefinsmetallalactones As Intmentioning

confidence: 99%

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

Hölscher

Gürtler

Keim

et al. 2012

Zeitschrift Für Naturforschung B

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Dedicated to Professor Heribert Offermanns on the occasion of his 75 th birthdayWith the growing perception of industrialized societies that fossil raw materials are limited resources, academic chemical research and chemical industry have started to introduce novel catalytic technologies which aim at the development of economically competitive processes relying much more strongly on the use of alternative carbon feedstocks. Great interest is given world-wide to carbon dioxide (CO 2 ) as it is part of the global carbon cycle, nontoxic, easily available in sufficient quantities anywhere in the industrialized world, and can be managed technically with ease, and at low cost. In principle carbon dioxide can be used to generate a large variety of synthetic products ranging from bulk chemicals like methanol and formic acid, through polymeric materials, to fine chemicals like aromatic acids useful in the pharmaceutical industry. Owing to the high thermodynamic stability of CO 2 , the energy constraints of chemical reactions have to be carefully analyzed to select promising processes. Furthermore, the high kinetic barriers for incorporation of CO 2 into C-H or C-C bond forming reactions require that any novel transformation of CO 2 must inevitably be associated with a novel catalytic technology. This short review comprises a selection of the most recent academic and industrial research developments mainly with regard to innovations in CO 2 chemistry in the field of homogeneous catalysis and processes.

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Oxanickelacyclopentene Derivatives from Nickel(0), Carbon Dioxide, and Alkynes

Abstract: The complete manuscript of this communication appears in: Angew. Chem. Suppl. 1982, 147. DOI:10.1002/anie.198201470

Cited by 102 publications

References 3 publications

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Ni- and Fe-catalyzed Carboxylation of Unsaturated Hydrocarbons with CO2

Carbon Dioxide as a Carbon Resource – Recent Trends and Perspectives

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