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Search for "rhodium" in Full Text gives 183 result(s) in Beilstein Journal of Organic Chemistry.

The chemistry of bisallenes

  • Henning Hopf and
  • Georgios Markopoulos

Beilstein J. Org. Chem. 2012, 8, 1936–1998, doi:10.3762/bjoc.8.225

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Published 15 Nov 2012

Rh(III)-catalyzed directed C–H bond amidation of ferrocenes with isocyanates

  • Satoshi Takebayashi,
  • Tsubasa Shizuno,
  • Takashi Otani and
  • Takanori Shibata

Beilstein J. Org. Chem. 2012, 8, 1844–1848, doi:10.3762/bjoc.8.212

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  • ; ferrocene; rhodium; Introduction Ferrocene and its derivatives are among the most useful organometallic compounds because of their chemical and thermal stabilities, structures, and redox activity [1][2]. One of the most remarkable applications of ferrocene derivatives is as chiral ligands [3][4]. A variety
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Published 29 Oct 2012

Evaluation of a chiral cubane-based Schiff base ligand in asymmetric catalysis reactions

  • Kyle F. Biegasiewicz,
  • Michelle L. Ingalsbe,
  • Jeffrey D. St. Denis,
  • James L. Gleason,
  • Junming Ho,
  • Michelle L. Coote,
  • G. Paul Savage and
  • Ronny Priefer

Beilstein J. Org. Chem. 2012, 8, 1814–1818, doi:10.3762/bjoc.8.207

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  • (MAO) inactivators [8][9][10]. Cubanes have also shown a propensity to undergo cage opening. In particular, syn-tricyclooctadienes are formed when rhodium(I) salts are introduced [11], while with silver(I) or palladium(II) catalysts, cuneane is obtained [12]. Spontaneous cage opening has been observed
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Published 22 Oct 2012

Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles

  • Rajkumar Jeyachandran,
  • Harish Kumar Potukuchi and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2012, 8, 1771–1777, doi:10.3762/bjoc.8.202

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  • ][16]. This streamlining of organic synthesis has predominantly been accomplished with palladium [4][5][6][7][8][9][10][11][12][13][14][15][16], rhodium [17][18][19] or ruthenium [20][21][22] complexes [4][5][6][7][8][9][10][11][12][13][14][15][16]. However, less expensive nickel, cobalt, iron or
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Published 16 Oct 2012

C2-Alkylation of N-pyrimidylindole with vinylsilane via cobalt-catalyzed C–H bond activation

  • Zhenhua Ding and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2012, 8, 1536–1542, doi:10.3762/bjoc.8.174

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  • as a directing group for rhodium-catalyzed C2-alkenylation [36], was entirely ineffective. Vinylsilanes bearing dimethylphenylsilyl and triphenylsilyl groups were amenable to the addition reaction with 1a, affording the adduct 3ab and 3ac in modest yields. Vinyltriethoxysilane also reacted with 1a in
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Published 14 Sep 2012

N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters

  • Takuya Uno,
  • Yusuke Kobayashi and
  • Yoshiji Takemoto

Beilstein J. Org. Chem. 2012, 8, 1499–1504, doi:10.3762/bjoc.8.169

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  • migration of the N-acyl glycine derivatives [18]. The other consists of C–N bond-forming reactions, such as (c) a rhodium-catalyzed N–H insertion reaction with α-diazo-β-keto esters [19][20][21], and (d) α-oxidation of β-keto esters to the corresponding oximes and the subsequent hydrogenation [22]. However
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Published 10 Sep 2012

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

  • Hervé Bricout,
  • Estelle Léonard,
  • Christophe Len,
  • David Landy,
  • Frédéric Hapiot and
  • Eric Monflier

Beilstein J. Org. Chem. 2012, 8, 1479–1484, doi:10.3762/bjoc.8.167

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  • substrates constitutes a real challenge not completely solved so far. Recently, we showed that an association of cyclodextrins (CDs) and amphiphilic phosphanes could significantly improve the catalytic performances in an aqueous rhodium-catalyzed hydroformylation of higher olefins [6]. Herein we clearly
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Published 06 Sep 2012

Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization

  • Hiroki Oguri,
  • Haruki Mizoguchi,
  • Hideaki Oikawa,
  • Aki Ishiyama,
  • Masato Iwatsuki,
  • Kazuhiko Otoguro and
  • Satoshi Ōmura

Beilstein J. Org. Chem. 2012, 8, 930–940, doi:10.3762/bjoc.8.105

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  • diazotransfer, leading to cyclization precursors. The rhodium-catalyzed tandem cyclization and divergent cycloaddition gave rise to tetracyclic and hexacyclic scaffolds by the appropriate choice of dipolarophiles installed at modules 3 and 4. A different piperidine-based manifold 15 bearing an amino group was
  • undertaken. Keywords: chemical diversity; divergent cyclization; indole alkaloids; modular assembly; rhodium-catalyzed cyclization–cycloaddition; skeletal and stereochemical diversity; Introduction Biologically intriguing natural products often possess cyclic scaffolds bearing dense arrays of functional
  • 3. Rhodium(II)-catalyzed tandem cyclization–cycloaddition [19][20][21] of the tetraketide-like precursors produced distinct multicyclic scaffolds, 4 and 5, differing in the relative orientations of the substructures. This approach illustrates a systematic way of diversifying skeletal arrays in a
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Published 22 Jun 2012

Intramolecular carbenoid ylide forming reactions of 2-diazo-3-keto-4-phthalimidocarboxylic esters derived from methionine and cysteine

  • Marc Enßle,
  • Stefan Buck,
  • Roland Werz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2012, 8, 433–440, doi:10.3762/bjoc.8.49

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  • three steps. Upon rhodium-catalysed dediazoniation, two intramolecular carbenoid reactions competed, namely the formation of a cyclic sulfonium ylide and that of a six-ring carbonyl ylide. The S-methyl and S-benzyl ylides 12a and b could be isolated, while S-allyl ylide 12c underwent a [2,3]-sigmatropic
  • undergo inter- and intramolecular formation of N-, O-, S- and other ylides [1][2]. The benefit of these transformations, which are usually performed with rhodium- or copper-based catalysts, is given by subsequent rearrangement or addition reactions of the reactive ylides; several recent reviews [3][4][5
  • racemisation. A sample of 8a, which was prepared from a slightly racemised sample of 6a (HPLC: 90:10 enantiomeric ratio of the derived methyl ester, which was prepared from 6a and dry methanol in the presence of excess chlorotrimethylsilane) on the latter route, had an enantiomeric ratio of 83:17. Rhodium
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Published 22 Mar 2012

Fifty years of oxacalix[3]arenes: A review

  • Kevin Cottet,
  • Paula M. Marcos and
  • Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

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  • . The oxacalix[3]arene also formed a complex with rhodium. Elemental analysis supported a composition incorporating the H–Rh–C=O fragment. 1H NMR indicated that this was threaded through the macrocyclic annulus, based on the presence of a peak at −9.70 ppm, and infrared analysis showed a carbonyl
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Published 07 Feb 2012

Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy

  • Iain Coldham,
  • Adam J. M. Burrell,
  • Hélène D. S. Guerrand,
  • Luke Watson,
  • Nathaniel G. Martin and
  • Niall Oram

Beilstein J. Org. Chem. 2012, 8, 107–111, doi:10.3762/bjoc.8.11

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  • substituent must be sufficient to allow a successful decarbonylation (in comparison with substrate 16), possibly due to the reduced ability of the amine nitrogen atom to coordinate to the rhodium complex. Conclusion The chemistry described here provides a method to prepare fused tricyclic products in which
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Published 18 Jan 2012

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines

  • Melinda Nonn,
  • Loránd Kiss,
  • Reijo Sillanpää and
  • Ferenc Fülöp

Beilstein J. Org. Chem. 2012, 8, 100–106, doi:10.3762/bjoc.8.10

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  •  3). Combinations of NaBH4 (as a mild and selective reducing agent) with cobalt, nickel, iridium or rhodium halide have previously been employed for cleavage of the isoxazoline ring system, which is otherwise inert to NaBH4 without such metal halide additives [50]. Accordingly, we investigated the
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Published 17 Jan 2012

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

  • Cécile Verrier,
  • Pierrik Lassalas,
  • Laure Théveau,
  • Guy Quéguiner,
  • François Trécourt,
  • Francis Marsais and
  • Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

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  • with arylboronic acids providing the arylazolylpalladium complex, which delivers the product (Scheme 27b and Scheme 28b). Rhodium- and nickel-catalyzed direct arylation of oxazoles with halides The methodology for the Rh(I)-catalyzed direct substitutive coupling of azoles with halides was developed by
  • )-catalyzed direct arylation of benzoxazole with arylboronic acids [76]; (a) procedure; (b) proposed mechanism. Ni(II)-catalyzed direct arylation of benzoxazoles with arylboronic acids under O2 [76]; (a) procedure; (b) proposed mechanism. Rhodium-catalyzed direct arylation of benzoxazole [78][79]. Ni(II
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Published 29 Nov 2011

Recent developments in gold-catalyzed cycloaddition reactions

  • Fernando López and
  • José L. Mascareñas

Beilstein J. Org. Chem. 2011, 7, 1075–1094, doi:10.3762/bjoc.7.124

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  • . Although transition metal-catalyzed cycloadditions have been known since the mid-20th century, it was not until the 80s and 90s that they were recognized as versatile and powerful synthetic tools. So far, most examples of transition metal-catalyzed cycloadditions have involved the use of rhodium, ruthenium
  • cycloadditions involving zwitterionic intermediates similar to I have also been developed with other transition metal catalysts such as tungsten, rhodium or platinum [32][33][34][35]. In particular, important developments were recently achieved with platinum catalysts [36][37], including the first
  • transformation is somewhat related to those previously described by Doyle and by Barluenga that involved α,β-unsaturated imines and rhodium–vinyl carbenoids (Doyle) or Fischer carbenes (Barluenga). However, the stereochemical outcome of these three processes is different [78][79]. Therefore, the reactivity of
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Published 09 Aug 2011

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

  • Alexandre Pradal,
  • Chung-Meng Chao,
  • Patrick Y. Toullec and
  • Véronique Michelet

Beilstein J. Org. Chem. 2011, 7, 1021–1029, doi:10.3762/bjoc.7.116

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  • chiral iridium catalyst [41] (Scheme 1, reaction 2). We and others recently pursued the improvement and development of this enantioselective process, by employing platinum [42][43][44], rhodium [45] or gold [46][47][48] complexes. Following our previous work with chiral gold catalysts [46], we report a
  • % isolated yield respectively) resulting from 5-exo- and 6-endo cycloisomerization reactions [20][66]. Thus, the gold catalytic system cannot compete with the results obtained for the cyclizations of nitrogen-tethered enynes in the presence of iridium, platinum or rhodium catalysts [41][42][43][44][45]. The
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Published 26 Jul 2011

Cationic gold(I) axially chiral biaryl bisphosphine complex-catalyzed atropselective synthesis of heterobiaryls

  • Tetsuro Shibuya,
  • Kyosuke Nakamura and
  • Ken Tanaka

Beilstein J. Org. Chem. 2011, 7, 944–950, doi:10.3762/bjoc.7.105

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  • -aryl-2-pyridones has already been achieved by rhodium catalyzed [2 + 2 + 2] cycloaddition [18], while the atropselective synthesis of 4-aryl-2-pyridones has not yet been realized. The application of this intramolecular hydroalkenylation reaction to the atropselective synthesis of 4-aryl-2-pyridones
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Published 06 Jul 2011

When cyclopropenes meet gold catalysts

  • Frédéric Miege,
  • Christophe Meyer and
  • Janine Cossy

Beilstein J. Org. Chem. 2011, 7, 717–734, doi:10.3762/bjoc.7.82

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  • cyclopropene for coordination to the gold catalyst (Scheme 13) [21][26]. The rearrangement of 27a to 28a (95%) had been previously reported by Müller et al. using rhodium(II) perfluorobutyrate as a catalyst (1 mol %, C6H6, reflux, 48 h) [32], whereas Padwa et al. showed that the isomerization of 27b to 28b was
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Published 30 May 2011

Gold-catalyzed naphthalene functionalization

  • Pedro J. Pérez,
  • M. Mar Díaz-Requejo and
  • Iván Rivilla

Beilstein J. Org. Chem. 2011, 7, 653–657, doi:10.3762/bjoc.7.77

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  • observed with other metal-based catalysts [4][5][6]. The above transformation with rhodium-based catalysts [7][8] has also been investigated with naphthalene as a substrate. In this case, Teyssié and co-workers showed that it could be converted, using t-butyl diazoacetate, into norcaradiene type
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Published 23 May 2011

Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes

  • Tomoya Miura,
  • Tsuneaki Biyajima,
  • Takeharu Toyoshima and
  • Masahiro Murakami

Beilstein J. Org. Chem. 2011, 7, 578–581, doi:10.3762/bjoc.7.67

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  • Tomoya Miura Tsuneaki Biyajima Takeharu Toyoshima Masahiro Murakami Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan 10.3762/bjoc.7.67 Abstract A rhodium(I)/dppe catalyst promoted dimerization of monosubstituted allenes in a
  • stereoselective manner to give cross-conjugated trienes, which are different from those obtained by a palladium catalyst. Keywords: allene; cross-conjugated triene; dimerization; rhodium; stereoselective; Introduction Cross-conjugated trienes, known as [3]dendralenes [1], are attractive synthetic precursors
  • substituted cross-conjugated trienes 2 in high yield (Scheme 1) [21]. We report here that dimerization of monosubstituted allenes is also catalyzed by a rhodium(I)/dppe complex to form cross-conjugated trienes 3, which are different from those obtained with the palladium catalyst. Results and Discussion We
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Published 09 May 2011

Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.01,5]dodecenone

  • Fuyuhiko Inagaki,
  • Naoya Itoh,
  • Yujiro Hayashi,
  • Yumi Matsui and
  • Chisato Mukai

Beilstein J. Org. Chem. 2011, 7, 404–409, doi:10.3762/bjoc.7.52

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  • tricyclo[6.4.0.01,5]dodecenone framework in a satisfactory yield. Keywords: allene; bicyclo[4.3.0] derivatives; carbonylative [2 + 2 + 1] cycloaddition; quaternary center construction; rhodium; Introduction The Co2(CO)8-mediated Pauson–Khand reaction (PKR) [1][2] is well recognized as a formal [2 + 2 + 1
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Published 07 Apr 2011

Rh-Catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles

  • Franca M. Cordero,
  • Carolina Vurchio,
  • Stefano Cicchi,
  • Armin de Meijere and
  • Alberto Brandi

Beilstein J. Org. Chem. 2011, 7, 298–303, doi:10.3762/bjoc.7.39

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  • )-catalyzed opening of the VCP moiety embedded in an azapolycyclic system occurs at high temperature (110–130 °C) to afford the corresponding 1,3-dienes in moderate yield (34–53%). Keywords: nitrogen heterocycles; rearrangement; rhodium; small ring systems; spiro compounds; Introduction The cyclopropyl
  • other interesting transformations, such as the [5 + 2] cycloadditions of vinylcyclopropanes to alkynes developed by Wender and co-workers [36][37]. It is known, that rhodium-catalyzed rearrangements of unactivated VCPs, without any functional substituent, usually afford dienes. In order to evaluate the
  • bond to form the intermediates C which can undergo metal hydride elimination or 1,3-hydride migration to the rhodium to give, respectively, the allyl- and alkylrhodium(III) hydride complexes D and F. Metal extrusion by reductive elimination leads to the observed dienes and regeneration of the catalyst
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Published 09 Mar 2011

Backbone tuning in indenylidene–ruthenium complexes bearing an unsaturated N-heterocyclic carbene

  • César A. Urbina-Blanco,
  • Xavier Bantreil,
  • Hervé Clavier,
  • Alexandra M. Z. Slawin and
  • Steven P. Nolan

Beilstein J. Org. Chem. 2010, 6, 1120–1126, doi:10.3762/bjoc.6.128

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  • phosphanes, and more recently, has been used to study the electronic properties of NHCs [34]. However, the high toxicity of [Ni(CO)4] encouraged the search for analogous systems using different metals to determine the TEP. One of the most popular and suitable alternatives to nickel is a rhodium carbonyl
  • parameters associated with these synthetic variations. Using a rhodium carbonyl system, the electronic variations brought about by substituents on the NHC lead to the following ligand electronic donor scale: IMesMe > IMes > IMesBr > IMesCl. The size of the substituent also affects the steric hindrance of the
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Published 23 Nov 2010

Recent advances in carbocupration of α-heterosubstituted alkynes

  • Ahmad Basheer and
  • Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

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  • adduct 29. However, the reaction was not completely stereoselective (Scheme 13) [25]. Although not a copper-mediated transformation, the rhodium-catalyzed carbozincation of ynamides should be noted since the regioselectivities were, in general, high (>19:1), though in some cases somewhat diminished with
  • Me2Zn (5:1) [26][27]. The rhodium-catalyzed annulation of ynamides with arylboron compounds containing an aldehyde or a ketone moiety have also been developed and lead to functionalized 2-amidoindenes with good levels of regioselectivity [28]. P-substituted alkynes Stereo- and regioselective
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Published 15 Jul 2010

Molecular recognition of organic ammonium ions in solution using synthetic receptors

  • Andreas Späth and
  • Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

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Published 06 Apr 2010

Concise methods for the synthesis of chiral polyoxazolines and their application in asymmetric hydrosilylation

  • Wei Jie Li,
  • Zun Le Xu and
  • Sheng Xiang Qiu

Beilstein J. Org. Chem. 2010, 6, No. 29, doi:10.3762/bjoc.6.29

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  • concomitant removal of water or the alcohol produced in the reaction. The method is much simpler and more efficient in comparison to those methods reported in the literature. The compounds were used as chiral ligands in the rhodium-catalyzed asymmetric hydrosilylation of aromatic ketones, and the effects of
  • the linkers and the substituents present on the oxazoline rings on the yield and enantioselectivity investigated. Compound 2 was identified as the best ligand of this family for the hydrosilylation of aromatic ketones. Keywords: aromatic ketone; hydrosilylation; polyoxazoline; rhodium; synthesis
  • –7) are described, which are much simpler and more efficient in comparison to those reported in the literature. With these chiral ligands as templates, the rhodium-catalyzed asymmetric hydrosilylation of aromatic ketones was carried out. The effects of the linkers of oxazoline rings and the
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Published 25 Mar 2010
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