Übergangsmetallkatalysierte Benzylierung von Arenen und Heteroarenen

Mertins, Kristin; Iovel, I.; Kischel, Jette; Zapf, Alexander; Beller, Matthias

doi:10.1002/ange.200460666

Cited by 52 publications

(6 citation statements)

References 65 publications

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“…In 2005 Beller et al systematically tested the activity of various Lewis- and Brønsted acids in FC benzylations. They found that late transition metals such as HAuCl 4 [ 23 ], IrCl 3 , [MesW(CO) 3 ], RhCl 3 , H 2 PdCl 4 , H 2 PtCl 6 [ 24 ] and FeCl 3 [ 25 ] were the most effective. FeCl 3 , in particular, is an attractive alternative to rare-earth triflates since it is non-toxic, cheap and readily available.…”

Section: Reviewmentioning

confidence: 99%

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

Rueping¹,

Nachtsheim²

2010

Beilstein J. Org. Chem.

604

353

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SummaryThe development of efficient Friedel–Crafts alkylations of arenes and heteroarenes using only catalytic amounts of a Lewis acid has gained much attention over the last decade. The new catalytic approaches described in this review are favoured over classical Friedel–Crafts conditions as benzyl-, propargyl- and allyl alcohols, or styrenes, can be used instead of toxic benzyl halides. Additionally, only low catalyst loadings are needed to provide a wide range of products. Following a short introduction about the origin and classical definition of the Friedel–Crafts reaction, the review will describe the different environmentally benign substrates which can be applied today as an approach towards greener processes. Additionally, the first diastereoselective and enantioselective Friedel–Crafts-type alkylations will be highlighted.

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Section: Reviewmentioning

confidence: 99%

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

Rueping¹,

Nachtsheim²

2010

Beilstein J. Org. Chem.

604

353

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show abstract

“…[30,[41][42][43][44][45][46][47][48][49][50][51][52][53] Beller and co-workers described two elegant benzylation reactions using a Friedel-Crafts arylation strategy of secondary benzyl derivatives with electron-rich arene nucleophiles. [54,55] A cobalt-catalyzed arylation of benzyl chloride derivatives with aryl zinc reagents has also been described. [49,50] In general, there is still a lack of efficient methods to build new CÀC bonds between secondary benzyl derivatives and arenes.…”

mentioning

confidence: 99%

Zinc Chloride Enhanced Arylations of Secondary Benzyl Trifluoroacetates in the Presence of β‐Hydrogen Atoms

et al. 2010

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“…(1)]. [38] In comparison with processes using H 2 SO 4 , AlCl 3 , metal complexes, [39][40][41] supported solid acids, [42,43] metal ion-incorporated zeolite catalysts, [44] complex oxides, [45,46] and Nafion membranes, [47] our method possesses the advantages of facile catalyst preparation, excellent catalytic performances and easy catalyst recycling and reuse.…”

Section: Introductionmentioning

confidence: 99%

High Catalytic Efficiency of Nanostructured Molybdenum Trioxide in the Benzylation of Arenes and an Investigation of the Reaction Mechanism

Wang

Ueda

2008

Chemistry A European J

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The synthesis and characterization of nanostructured MoO(3) with a thickness of about 30 nm and a width of about 450 nm are reported. The composition formula of the MP (precipitation method) precursor was estimated to be [(NH(4))(2)O](0.169) x MoO(3) x (H(2)O)(0.239). The calcination of the precursor in air afforded nanostructured pellets of the alpha-MoO(3) phase. The nanostructured MoO(3) catalyst exhibited high efficiency in catalyzing the benzylation of various arenes with substituted benzyl alcohols, which were strikingly different to common bulk MoO(3). Most reactions offered >99% conversion and >99% selectivity to monoalkylated compounds. MoO(3) is a typical acid catalyst. However, the benzylation reaction over nanostructured MoO(3) does not belong to the acid-catalyzed type or defect site-catalyzed type, since the catalyst has no acidity and defect site on surface. Characterization with thermal, spectroscopic, and electronic techniques reveal that the catalyst contains fully oxygen-coordinated MoO(6) octahedrons on the surface but partially reduced species (Mo(5+)) within the bulk phase. The terminal oxygen atoms of Mo=O bonds on the (010) basal plane resemble oxygen anion radicals and act as active sites for the adsorption and activation of benzyl alcohols by electrophilic attack. Such sites are indispensable for catalytic reactions since the blocking of these sites by electron acceptors, such as tetracyanoethylene (TCNE), can greatly decrease catalytic activity. This work represents a successful example of combining a heterogeneous catalysis study with nanomaterial synthesis.

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Übergangsmetallkatalysierte Benzylierung von Arenen und Heteroarenen

Cited by 52 publications

References 65 publications

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysis

Zinc Chloride Enhanced Arylations of Secondary Benzyl Trifluoroacetates in the Presence of β‐Hydrogen Atoms

High Catalytic Efficiency of Nanostructured Molybdenum Trioxide in the Benzylation of Arenes and an Investigation of the Reaction Mechanism

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