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Search for "metal-catalyzed" in Full Text gives 404 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

  • Amrita Das,
  • Mitasree Maity,
  • Simon Malcherek,
  • Burkhard König and
  • Julia Rehbein

Beilstein J. Org. Chem. 2018, 14, 2520–2528, doi:10.3762/bjoc.14.228

Graphical Abstract
  • , antidepressant or antileukotriene agents (Figure 1). Three of the five most selling drugs in 2015 were organosulfur compounds. The majority of methods for C–S bond synthesis use transition metal-catalyzed cross coupling of thiols and their derivatives with organohalides [4][5][6], arylboronic acids [7], aryl
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Published 27 Sep 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

Graphical Abstract
  • -Doctoral Fellow at the KU Leuven, Belgium under the EMINTE programme. During post-doctoral work his research work was related to organic synthesis under microwave reaction conditions. Presently, he is Research Associate with Prof. S. Kotha. His research interests include various transition-metal-catalyzed
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Published 21 Sep 2018

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

  • Tetsuaki Fujihara and
  • Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

Graphical Abstract
  • reagents in transition-metal-catalyzed C–C bond-forming reactions [21][22][23]. In particular, the carboxylation of allyl esters with CO2 has been catalyzed by Pd or Ni under electrochemical reaction conditions [24][25]. For catalytic reactions using reducing agents, Martin reported Ni-catalyzed
  • useful methods such as the transition-metal-catalyzed carbozincation of alkynes that affords stereodefined alkenylzinc compounds have been developed. To date, a variety of organozinc reagents (RZnX and R2Zn: R = aryl, alkyl, alkenyl, alkynyl, allyl, and benzyl groups) have been used in these reactions
  • ). Possibly another ligand exchange between E and KOAc regenerates the Rh complex A (step e). The desired product (35) is obtained after lactonization. Hydrocarboxylation of arylalkenes Hydrocarboxylation is an essential carboxylation reaction. To date, transition-metal-catalyzed hydrocarboxylation reactions
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Published 19 Sep 2018

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

  • Henrike Ehrhorn,
  • Janin Schlösser,
  • Dirk Bockfeld and
  • Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

Graphical Abstract
  • progress in the past decades [1][2][3][4][5], the synthetic potential of alkyne metathesis has been growing only recently [6][7][8][9][10][11]. Alkyne metathesis represents a transition-metal-catalyzed transformation in which carbon–carbon triple bonds are cleaved and formed under mild conditions via
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Published 18 Sep 2018

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

  • Lu Yang,
  • Yuwei Wu,
  • Yiming Yang,
  • Chengping Wen and
  • Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

Graphical Abstract
  • is a heterocyclic moiety showing exceptionally broad and important applications as privileged structure in the discovery of biologically functional scaffolds, organic materials preparation, as directing group in transition-metal-catalyzed transformations and as key building block in the synthesis of
  • ][30][31][32], for example, has served enormously to the advances in both the preparation and application of 1,2,3-triazoles. In addition, the discovery of other metal-catalyzed alkyne–azide cycloadditions (MAAC) providing 1,2,3-triazoles with diverse substitution patterns triggers the continuous
  • development of these metal-catalyzed cycloaddition strategies [33][34][35]. Alongside the vast progress happened in MAAC-based 1,2,3-triazole synthesis, the past decade has witnessed the emergence of another powerful cycloaddition tool for the 1,2,3-triazole synthesis: the metal-free cycloaddition of azides
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Published 07 Sep 2018

Hydroarylations by cobalt-catalyzed C–H activation

  • Rajagopal Santhoshkumar and
  • Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

Graphical Abstract
  • synthesis owing to the necessity of green chemistry for the modern universe [1][2][3]. In this context, catalytic C–H functionalization has been acknowledged as an atom- and step-economical process [4][5][6]. A wide range of transition metal-catalyzed non-directed or directing group assisted C–H activation
  • -catalyzed hydroarylation of C=X bonds Transition-metal-catalyzed addition of C–H bond to polar π bonds such as imines, isocyanates and carbonyls is one of the efficient methods to incorporate heteroatoms in organic molecules [45]. Yoshikai et al. developed an addition reaction of arylpyridines 3 to imines
  • traditional synthetic methods to construct new C−C bonds. Among the first-row transition metals, both low- and high-valent cobalt catalysts have played a substantial role in these hydroarylation reactions providing an economical alternative to the precious metal-catalyzed reactions and also showed distinct
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Published 29 Aug 2018

Studies towards the synthesis of hyperireflexolide A

  • G. Hari Mangeswara Rao

Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

Graphical Abstract
  • 5 could not only act as a surrogate for C-9 carbonyl but also facilitate installation of an angular methyl group. The retrosynthetic analysis for hyperireflexolide A is depicted in Scheme 1. We envisioned that hyperireflexolide A (1) could be synthesized by metal-catalyzed opening of the epoxide 2
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Published 13 Aug 2018

Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

  • Jiao-Na Han,
  • Cong Du,
  • Xinju Zhu,
  • Zheng-Long Wang,
  • Yue Zhu,
  • Zhao-Yang Chu,
  • Jun-Long Niu and
  • Mao-Ping Song

Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

Graphical Abstract
  • methods always possess some limitations such as preactivated starting materials, poor regioselectivities, and tedious steps [5]. Therefore, it is desirable to develop an effective strategy to achieve this transformation [6][7]. Over the past few decades, transition-metal-catalyzed C–H activation to form C
  • ][35][36][37][38][39][40][41][42] have successfully reported alkoxylation reactions with the auxiliary of directing groups. However, the transition-metal-catalyzed C–H alkoxylation is still largely limited to palladium- [28][33][34][35][36][37][38][39][40] or copper- [26][27][29][41][42] catalyzed
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Published 09 Aug 2018

D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

  • Michael R. Imrich,
  • Jochen Kraft,
  • Cäcilia Maichle-Mössmer and
  • Thomas Ziegler

Beilstein J. Org. Chem. 2018, 14, 2082–2089, doi:10.3762/bjoc.14.182

Graphical Abstract
  • solvent) the reaction proceeded smoothly in good to high yields. We chose 2-bromobenzonitrile (8) as a nucleophile because we planned to modify the aryl bromide by transition metal-catalyzed cross-coupling reactions afterwards. Unfortunately, the nitrile must be used in a high excess of 15 equiv because
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Published 08 Aug 2018

Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

  • Xiang Li,
  • Pinhong Chen and
  • Guosheng Liu

Beilstein J. Org. Chem. 2018, 14, 1813–1825, doi:10.3762/bjoc.14.154

Graphical Abstract
  • under metal-catalyzed conditions, due to the high affinity of the diamine products to metal catalysts. Thus an iodoarene-catalyzed strategy provides a valuable alternative way to the diamination of alkenes. Recently, Muñiz and co-workers reported a chiral iodoarene-catalyzed intermolecular diamination
  • . Compared to the diverse reactivity profiles of transition metal-catalyzed functionalization of alkenes, hypervalent iodine (III)-mediated reactions are limited to nucleophilic substitution processes. Recently, Liu and co-workers reported a novel cooperative strategy by combining palladium catalysis and
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Published 18 Jul 2018

Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

  • Eric Detmar,
  • Valentin Müller,
  • Daniel Zell,
  • Lutz Ackermann and
  • Martin Breugst

Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

Graphical Abstract
  • ][10][11], London dispersion can also play a crucial role in different transition-metal-catalyzed reactions [12][13][14][15][16][17]. The C–H-rich di-1-adamantylphosphine oxide – a typical dispersion element – was experimentally found to be an excellent preligand for ruthenium- and palladium-catalyzed
  • exclusively act as a sterically demanding ligand in transition-metal-catalyzed reactions. Conclusion We have analyzed the cobalt(III)-catalyzed C–H cyanation of differently substituted 2-phenylpyridines with N-cyano-N-aryl-p-toluenesulfonamide using density functional theory. On the basis of our computational
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Published 25 Jun 2018

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

  • Gwendal Grelier,
  • Benjamin Darses and
  • Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

Graphical Abstract
  • , their reactivity is higher than that of the corresponding aryl halides, a property that has been widely exploited to develop efficient transition-metal-catalyzed cross coupling reactions [55]. The latter, however, allow for transferring only one of the two aromatic motifs of the iodonium reagents
  • reductive elimination. Starting from the ortho-N-(acyl)diaryl-λ3-iodanes 57, a combination of copper and palladium catalysis, in the presence of a phosphine ligand, induces the internal O-arylation of the proximal amide moiety, followed by a subsequent metal-catalyzed coupling-reaction with the resulting Ar
  • -arylation of carbonyl compounds In addition to their role as aryl donors in numerous metal-catalyzed couplings, diaryl-λ3-iodanes are also relevant reagents to perform the α-arylation of enolates. However, the reaction is again limited to the transfer of a single aryl group. As an alternative to address
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Published 21 Jun 2018

Metal-free formal synthesis of phenoxazine

  • Gabriella Kervefors,
  • Antonia Becker,
  • Chandan Dey and
  • Berit Olofsson

Beilstein J. Org. Chem. 2018, 14, 1491–1497, doi:10.3762/bjoc.14.126

Graphical Abstract
  • recently, Bolm and co-workers reported a metal-free cyclization of iodo-substituted diaryl ethers with a broad scope (Scheme 1b) [18]. Transition metal-catalyzed cross couplings have also been employed to form the required C–O and C–N bonds, e.g., by Cu-catalyzed cyclization of 2-(2-bromophenoxy)anilines
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Published 20 Jun 2018

Three-component coupling of aryl iodides, allenes, and aldehydes catalyzed by a Co/Cr-hybrid catalyst

  • Kimihiro Komeyama,
  • Shunsuke Sakiyama,
  • Kento Iwashita,
  • Itaru Osaka and
  • Ken Takaki

Beilstein J. Org. Chem. 2018, 14, 1413–1420, doi:10.3762/bjoc.14.118

Graphical Abstract
  • organometallics, involving a wide range of transition metal-catalyzed reactions. For example, transmetalation between an organonickel (or organocobalt) complex and chromium salt results in the formation of a highly nucleophilic organochromium species, which enables efficient addition to aldehydes to give
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Published 11 Jun 2018

Recent applications of chiral calixarenes in asymmetric catalysis

  • Mustafa Durmaz,
  • Erkan Halay and
  • Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

Graphical Abstract
  • reaction. In these reactions, calixarenes are used either as ligands in metal-catalyzed reactions or as organocatalysts. The application of inherently chiral calixarenes as chiral catalysts is still quite scarce, except in aldol, Michael and Henry reactions. Asymmetric catalysis with chiral calixarenes in
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Published 08 Jun 2018

Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines

  • Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 1349–1369, doi:10.3762/bjoc.14.114

Graphical Abstract
  • , ECA109 and BT474 cancer cell lines. Metal-catalyzed reactions In addition to organocatalysts, chiral metal catalysts [41][42][43][44][45][46][47] have been recently applied to promote enantioselective Mannich reactions. As an example, in 2015 Feng et al. reported the enantioselective Mannich reaction of
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Published 06 Jun 2018

[3 + 2]-Cycloaddition reaction of sydnones with alkynes

  • Veronika Hladíková,
  • Jiří Váňa and
  • Jiří Hanusek

Beilstein J. Org. Chem. 2018, 14, 1317–1348, doi:10.3762/bjoc.14.113

Graphical Abstract
  • by Taran et al. [4]. In order to avoid duplication our review is therefore focused in more detail on thermal, photochemical as well as metal-catalyzed reactions of sydnones with alkynes and factors that influence the yield and ratio of both possible regioisomers and also the kinetics and mechanism of
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Published 05 Jun 2018

Atom-economical group-transfer reactions with hypervalent iodine compounds

  • Andreas Boelke,
  • Peter Finkbeiner and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

Graphical Abstract
  • lead to an overall AE of up to 70% but also produces synthetically versatile intermediates for subsequent transformations, in particular metal-catalyzed cross-coupling reactions. If benziodoxolones or benziodoxoles are used as group-transfer reagents, nearly 100% AE is possible since the counterion
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Published 30 May 2018

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

  • Anna Czarnecka,
  • Emilia Kowalska,
  • Agnieszka Bodzioch,
  • Joanna Skalik,
  • Marek Koprowski,
  • Krzysztof Owsianik and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

Graphical Abstract
  • the key substrates for aromatic cyclodehydration, also known as the Bradsher reaction [15], which leads to fused, polycyclic aromatic hydrocarbons [16][17][18][19]. This type of reaction found applications in synthesis of organic, optoelectronic materials [20][21][22]. Metal-catalyzed cross-coupling
  • ) has been performed. It is important for the sulfur-containing substrates for which metal-catalyzed cross-coupling reactions fail. The dibenzylic OH group has been preferentially reduced with the ZnI2/Na(CN)BH3 system in the presence of an ortho-dithioacetal moiety to give ortho-1,3-dithianylaryl(aryl
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Published 29 May 2018

Rhodium-catalyzed C–H functionalization of heteroarenes using indoleBX hypervalent iodine reagents

  • Erwann Grenet,
  • Ashis Das,
  • Paola Caramenti and
  • Jérôme Waser

Beilstein J. Org. Chem. 2018, 14, 1208–1214, doi:10.3762/bjoc.14.102

Graphical Abstract
  • ), which ends up on the pyridinone ring. As alternative, a Suzuki–Miyaura coupling between 3-halogenoindoles and (2-methoxypyridyl)boronic acids followed by a deprotection of the methoxy group [7][8] or transition-metal-catalyzed annulation methods [9] have also been reported. In contrast, several
  • (III) catalyst for C-5 and C-6 functionalization, respectively [13]. Hypervalent iodine reagents in general [20], and benziodoxole derivatives in particular [21], have found broad application in synthetic chemistry. Aryl iodonium salts have been used successfully in transition-metal-catalyzed
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Published 25 May 2018

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

  • Natalia Soldatova,
  • Pavel Postnikov,
  • Olga Kukurina,
  • Viktor V. Zhdankin,
  • Akira Yoshimura,
  • Thomas Wirth and
  • Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 849–855, doi:10.3762/bjoc.14.70

Graphical Abstract
  • nucleophiles including electron-rich carbon-centered species [5][6][7]. The unique arylating reactivity of diaryliodonium salts has been demonstrated in many metal-catalyzed and also metal-free transformations [8][9][10][11][12][13][14][15]. The development of novel synthetic approaches to diaryliodonium salts
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Published 12 Apr 2018

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

  • Zhensheng Zhao and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

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  • - and vinyl chlorides are highly sought-after intermediates for effecting allylations, and for use in transition metal-catalyzed carbon–carbon and carbon–heteroatom bond-forming reactions [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. Given the versatility of allyl chloride and β
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Published 09 Apr 2018

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

  • Jingbo Yu,
  • Zikun Hong,
  • Xinjie Yang,
  • Yu Jiang,
  • Zhijiang Jiang and
  • Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

Graphical Abstract
  • transition-metal-catalyzed reactions [1][2], which has shown itself as a powerful synthetic tool in both academic and industrial practice [3][4][5][6][7]. The transformation has been enrolled as key steps for numerous synthetic routes, including the recent President Green Chemistry Award winner route of
  • interesting substrates for industrial applications [11][12], possessing the characteristics of lower cost, easier to obtain and stable to store, they face the problem of dehalogenations especially under metal-catalyzed reactions [8][13][14][15][16][17][18], affecting the reaction yield and selectivity
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Published 06 Apr 2018

Cobalt-catalyzed directed C–H alkenylation of pivalophenone N–H imine with alkenyl phosphates

  • Wengang Xu and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2018, 14, 709–715, doi:10.3762/bjoc.14.60

Graphical Abstract
  • alkenylation reaction of pivalophenone N–H imine with an alkenyl phosphate. The reaction tolerates various substituted pivalophenone N–H imines as well as cyclic and acyclic alkenyl phosphates. Keywords: alkenylation; C–C bond formation; C–H activation; cobalt; imine; Introduction Transition-metal-catalyzed
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Published 28 Mar 2018

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills

  • Zi Liu,
  • Hui Xu and
  • Guan-Wu Wang

Beilstein J. Org. Chem. 2018, 14, 430–435, doi:10.3762/bjoc.14.31

Graphical Abstract
  • construction of C–X bonds. With the development of transition-metal-catalyzed cross-coupling reactions, a series of halogenations at the ortho-position of the directing groups have been disclosed [5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Nevertheless, from the viewpoint of green chemistry, the
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Published 16 Feb 2018
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