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Search for "metal catalysis" in Full Text gives 128 result(s) in Beilstein Journal of Organic Chemistry.

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

  • Sebastian Krüger and
  • Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

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  • give intermediate vinyl-allenecyclopropane 249, followed by a DVCPR to furnish cycloheptadiene 250. 1,2-Shift and vinyl-carbenoid formation sequences Two major pathways to generate divinylcyclopropanes using transition metal catalysis have been developed. Uemura and coworkers [204] were the first to
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Published 16 Jan 2014

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

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Published 15 Nov 2013

An investigation of the observed, but counter-intuitive, stereoselectivity noted during chiral amine synthesis via N-chiral-ketimines

  • Thomas C. Nugent,
  • Richard Vaughan Williams,
  • Andrei Dragan,
  • Alejandro Alvarado Méndez and
  • Andrei V. Iosub

Beilstein J. Org. Chem. 2013, 9, 2103–2112, doi:10.3762/bjoc.9.247

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  • transition metal catalysis [5][6][7][8] and as resolving agents [9]. Despite their high demand, the ability to produce structurally diverse chiral amines has not kept pace. Spurred by this shortcoming, innovative and improved chemical methods have been developed over the last fifteen years. Among them
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Published 15 Oct 2013

Post-Ugi gold-catalyzed diastereoselective domino cyclization for the synthesis of diversely substituted spiroindolines

  • Amit Kumar,
  • Dipak D. Vachhani,
  • Sachin G. Modha,
  • Sunil K. Sharma,
  • Virinder S. Parmar and
  • Erik V. Van der Eycken

Beilstein J. Org. Chem. 2013, 9, 2097–2102, doi:10.3762/bjoc.9.246

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  • materials. Based on this work and our continuous interest in transition metal catalysis [45][46][47][48][49][50][51][52][53][54], multicomponent reactions [55][56][57] and the chemistry of the indole core [58][59][60], we herein report a post-Ugi gold-catalyzed intramolecular domino cyclization sequence for
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Published 14 Oct 2013

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

  • Lucio Melone and
  • Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

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  • the O2-mediated selective oxidation of organic compounds and looking for environmentally safe alternatives to metal catalysis. Keywords: autoxidation; free-radicals; metal-free; molecular oxygen; N-hydroxyphthalimide; Introduction The development of efficient and cheap catalytic systems for the
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Published 02 Jul 2013

Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

  • Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143

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  • reactions such as nucleophilic substitution of P–X compounds with organometallic reagents, nucleophilic substitution of alkyl halides with phosphorus nucleophiles, and nucleophilic addition to polar unsaturated bonds. Recent advances in transition-metal catalysis have realized catalytic cross-coupling
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Published 28 Jun 2013

Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach

  • Sandeep Kumar,
  • Ramendra Pratap,
  • Abhinav Kumar,
  • Brijesh Kumar,
  • Vishnu K. Tandon and
  • Vishnu Ji Ram

Beilstein J. Org. Chem. 2013, 9, 809–817, doi:10.3762/bjoc.9.92

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  • /Heck reaction starting from N-acryloylanilides [38]. The use of metal catalysis, especially of palladium, has played a major role in the construction of 3-alkenylindolin-2-ones [38]. Despite significant progress in approaches for the construction of 3-alkenylindolin-2-ones, use of complicated
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Published 25 Apr 2013

Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

  • Martina Bonsignore,
  • Maurizio Benaglia,
  • Laura Raimondi,
  • Manuel Orlandi and
  • Giuseppe Celentano

Beilstein J. Org. Chem. 2013, 9, 633–640, doi:10.3762/bjoc.9.71

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  • nitrogen atom of the imine [24][25][26]. However, we were attracted by a recent work by Arndtsen, who demonstrated that coupling metal catalysis and the ability of amino acids to form hydrogen bonds provides an easy route for inducing both enantioselectivity and selectivity (left picture in Figure 3) [27
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Published 02 Apr 2013

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

  • Silvia M. Soria-Castro and
  • Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

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  • compounds. The formation of C–S bonds can also be accomplished in good to excellent yields by transition-metal catalysis [10][11], mainly using palladium [12], copper [13][14][15][16], nickel [17][18] and iron [19][20] salts. Aryl coupling reactions employing different palladium species as catalysts
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Published 04 Mar 2013

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

  • Adam Mondrzyk,
  • Beate Mondrzik,
  • Sabrina Gingter and
  • Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

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  • condensation. Alternative methods include electrochemical polymerization, metal catalysis or treatment with enzymes, which lead to phenyl–phenyl connected polyphenols [2][3][4][5]. In particular, oxidoreductase enzymes have the great advantage of nontoxicity and regioselective phenol–phenol coupling [6][7][8
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Published 04 Dec 2012

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

  • Zhi-Cong Geng,
  • Jian Chen,
  • Ning Li,
  • Xiao-Fei Huang,
  • Yong Zhang,
  • Ya-Wen Zhang and
  • Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

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  • synthesis of pyrazolidine derivatives by Wolfe et al. [33]. In the past decade, the research area of organocatalysis has grown rapidly and become a third brand of catalysis besides the well-established biocatalysis and metal catalysis [34][35][36][37][38][39][40][41][42][43][44]. Particularly
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Published 09 Oct 2012

Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis

  • Marcus Frings,
  • Isabelle Thomé and
  • Carsten Bolm

Beilstein J. Org. Chem. 2012, 8, 1443–1451, doi:10.3762/bjoc.8.164

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  • diastereoselective transformations or as chiral ligands in enantioselective metal catalysis [25][26][27][28][29][30][31][32][33]. With respect to the latter field we have recently demonstrated that various ligands bearing a sulfonimidoyl moiety lead to excellent stereoselectivities in transition metal-catalyzed
  • . They involve both metal catalysis [64][65] as well as organocatalysis. In the latter field, chiral phosphoric acids [66][67], bicyclic diamines [68], bifunctional thioureas [69], proline ester salts [70], pyrrolidinyl tetrazoles [71], and a quinine-derived amine [72] were reported to catalyze the
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Published 03 Sep 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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  • in this article. Methodologies, selectivity, mechanism and future aspects are presented. Keywords: ate complex; catalytic direct arylation; mechanism; oxazole; selectivity; transition-metal catalysis; Introduction Deprotonative metalation of aromatics is widely used as a powerful method for
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Published 29 Nov 2011

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation–decarbonylative alkynylation–cyclocondensation sequences

  • Charlotte F. Gers,
  • Julia Rosellen,
  • Eugen Merkul and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1173–1181, doi:10.3762/bjoc.7.136

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  • traditional multistep syntheses. Thus, they can be considered to be economically and ecologically efficient [9][10]. In particular, multicomponent syntheses of heterocycles initiated by transition metal catalysis received increasing attention in the past decade [11]. As a one-pot synthetic methodology, this
  • novel concept combines the unique reactivity patterns of transition metal catalysis with fundamental organic reactivity, in a sequential or consecutive fashion. Over the years, we have contributed to this concept through Pd/Cu-catalyzed accesses to enones and ynones and the in situ transformation of
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Published 26 Aug 2011

Efficient gold(I)/silver(I)-cocatalyzed cascade intermolecular N-Michael addition/intramolecular hydroalkylation of unactivated alkenes with α-ketones

  • Ya-Ping Xiao,
  • Xin-Yuan Liu and
  • Chi-Ming Che

Beilstein J. Org. Chem. 2011, 7, 1100–1107, doi:10.3762/bjoc.7.126

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  • molecules. Disappointingly, no conversion was observed when (t-Bu)2(o-diphenyl)PAuOTf only was used as the catalyst. Since dual-metal-catalysis is of interest from the perspective of unique reactivity [26][27][28][29][30][31][32][33][34][35][36][37][38][39][40], we explored a new cascade reaction involving
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Published 11 Aug 2011

Continuous gas/liquid–liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination

  • Jessica R. Breen,
  • Graham Sandford,
  • Dmitrii S. Yufit,
  • Judith A. K. Howard,
  • Jonathan Fray and
  • Bhairavi Patel

Beilstein J. Org. Chem. 2011, 7, 1048–1054, doi:10.3762/bjoc.7.120

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  • formation by base catalysis, by metal catalysis or by fluorination of appropriate pre-formed enol derivatives, such as trimethylsilyl enols or enol acetate derivatives [13][14]. Dicarbonyl systems are, of course, widely used for the construction of heterocyclic ring systems such a pyrimidine, pyridazine and
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Published 02 Aug 2011

Multicomponent reactions

  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 960–961, doi:10.3762/bjoc.7.107

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  • lead structures of active agents, catalysts and even novel molecule-based materials. This Thematic Series on multicomponent reactions represents a snapshot of a highly dynamic field and spans a broad range, from recent advances in isonitrile-based MCR to transition metal catalysis in MCR; from peptidic
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Published 13 Jul 2011

Highly efficient gold(I)-catalyzed Overman rearrangement in water

  • Dong Xing and
  • Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785, doi:10.3762/bjoc.7.88

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  • allylic trichloroacetimidates to allylic trichloroacetamides (Overman rearrangement) is a powerful and attractive strategy for the synthesis of allylic amines from readily available allylic alcohols [1][2]. This transformation can be conducted thermally at high temperatures or by transition metal
  • catalysis under very mild conditions [3][4][5][6][7]. Asymmetric induction has been achieved with certain types of transition metal catalysts (e.g., palladium complexes) in combination with chiral ancillary ligands [8][9][10][11][12][13]. However, although a large number of late transition metal catalysts
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Published 08 Jun 2011

Continuous flow hydrogenation using polysilane-supported palladium/alumina hybrid catalysts

  • Hidekazu Oyamada,
  • Takeshi Naito and
  • Shū Kobayashi

Beilstein J. Org. Chem. 2011, 7, 735–739, doi:10.3762/bjoc.7.83

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  • and substantially increase production. We also recently reported novel transition metal catalysis involving the immobilization of Pd or Pt onto polysilane supports by the microencapsulation method [12]. The Pd catalyst (Pd/PSi) had high activity with no or very little leaching of Pd, and it could be
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Published 31 May 2011

Unusual behavior in the reactivity of 5-substituted-1H-tetrazoles in a resistively heated microreactor

  • Bernhard Gutmann,
  • Toma N. Glasnov,
  • Tahseen Razzaq,
  • Walter Goessler,
  • Dominique M. Roberge and
  • C. Oliver Kappe

Beilstein J. Org. Chem. 2011, 7, 503–517, doi:10.3762/bjoc.7.59

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  • steel or Hastelloy coils are heated by conductive techniques. Through a series of control experiments, effects of homogeneous metal catalysis as a result of reactor corrosion, and heterogeneous catalytic effects derived from the large metal surface area in the microreactor environment (wall effects
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Published 21 Apr 2011
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  • , arylsulfonyl chlorides and arenediazonium salts with arylboronic acids that gave biaryls in good to excellent yields [28][31][32]. As part of our ongoing investigations aimed at the development of transition metal catalysis, we report here that the Suzuki–Miyaura cross-couplings of 1-aryltriazenes with
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Published 28 Jun 2010

A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

  • Kay M. Brummond and
  • Joshua M. Osbourn

Beilstein J. Org. Chem. 2010, 6, No. 33, doi:10.3762/bjoc.6.33

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  • rearrangement of the propargyl acetate 9a using transition metal catalysis (AuCl3 10 mol %, toluene, 1 h, rt) led to hydrolysis of the allenyl acetate functionality. This densely functionalized alkylidene cyclobutene 10a is postulated to arise via the [2 + 2] cycloaddition reaction between the alkyne and the
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Preliminary Communication
Published 08 Apr 2010

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

  • Magnus Rueping and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2010, 6, No. 6, doi:10.3762/bjoc.6.6

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  • % [Rh(cod)2]BF4, 4 mol% PPh3 and HBF4•OEt2 was necessary for sufficient reactivity; yet electron-rich and N-alkylated anilines react without a metal catalysis in the presence of catalytic amounts of HBF4 (Scheme 20). About the same time a Ru3(CO)12-catalyzed hydroarylation of anilines was reported as
  • simultaneously, an acid-catalyzed ortho-arylation of aniline employing the strong Brønsted acid PhNH3B(C6F5)4•Et2O was developed by Bergman et al. indicating the close relationship between strong Brønsted acid- and transition-metal catalysis [70]. A double ortho-hydroarylation of anilines with styrenes was
  • optical active ligands for enantioselective transition-metal catalysis (Scheme 22) [71]. To the best of our knowledge, efficient ortho-benzylations of anilines with benzyl alcohols as alkylating reagents have yet to be described [15]. Catalytic Friedel–Crafts allylations Allylated arenes represent
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Published 20 Jan 2010

Can we measure catalyst efficiency in asymmetric chemical reactions? A theoretical approach

  • Shaimaa El-Fayyoumy,
  • Matthew H. Todd and
  • Christopher J. Richards

Beilstein J. Org. Chem. 2009, 5, No. 67, doi:10.3762/bjoc.5.67

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  • chemistry [1]. Enormous progress has been made in recent years, most notably in homogenous transition metal catalysis, organocatalysis and enzyme-catalysed reactions. It is therefore surprising that there is no generally accepted measure for the effectiveness of a catalytic reaction. That is to say when we
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Published 19 Nov 2009

DBFOX- Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

  • Takehisa Ishimaru,
  • Norio Shibata,
  • Dhande Sudhakar Reddy,
  • Takao Horikawa,
  • Shuichi Nakamura and
  • Takeshi Toru

Beilstein J. Org. Chem. 2008, 4, No. 16, doi:10.3762/bjoc.4.16

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  • ) ligands, Box-Ph [(S,S)-2,2'-isopropylidene-bis(4-phenyl-2-oxazoline)] and DBFOX-Ph [(R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline)] [33][34][36]. As an extension of this study, we herein evaluate our DBFOX-Ph/metal catalysis for the enantioselective fluorination of 3-(2-arylacetyl)-2
  • stirred overnight under the same fluorination conditions. Further studies to improve the enantioselectivity of DBFOX-Ph/metal catalysis in enantioselective fluorination are under way. Structures of DBFOX-Ph, Box-Ph and NFSI. Transition-State Structure for the DBFOX-Ph/Ni(II) Catalyzed Enantioselective
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Published 20 May 2008
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