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Search for "Buchwald–Hartwig" in Full Text gives 65 result(s) in Beilstein Journal of Organic Chemistry.

Tuning of tetrathiafulvalene properties: versatile synthesis of N-arylated monopyrrolotetrathiafulvalenes via Ullmann-type coupling reactions

  • Vladimir A. Azov,
  • Diana Janott,
  • Dirk Schlüter and
  • Matthias Zeller

Beilstein J. Org. Chem. 2015, 11, 860–868, doi:10.3762/bjoc.11.96

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  • excess cannot be considered a disadvantage of the method. Additionally, use of the inexpensive Cu(I) catalyst allows to avoid BuchwaldHartwig amination [24][25], which employs more expensive Pd-based catalysts for a similar type of C–N coupling reactions. In a typical procedure, 1 equiv of MPTTF 7a, 7b
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Published 21 May 2015

Redox active dendronized polystyrenes equipped with peripheral triarylamines

  • Toshiki Nokami,
  • Naoki Musya,
  • Tatsuya Morofuji,
  • Keiji Takeda,
  • Masahiro Takumi,
  • Akihiro Shimizu and
  • Jun-ichi Yoshida

Beilstein J. Org. Chem. 2014, 10, 3097–3103, doi:10.3762/bjoc.10.326

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  • examined before studying the functionalization of dendronized polystyrene. Thus, di(p-methoxyphenyl)amino groups were introduced to 4 using a BuchwaldHartwig amination [11]. The choice of a base is crucial for this transformation, and the transformation was successfully carried out using Cs2CO3 as a base
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Published 22 Dec 2014

Exploration of C–H and N–H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines

  • Michael Ghobrial,
  • Marko D. Mihovilovic and
  • Michael Schnürch

Beilstein J. Org. Chem. 2014, 10, 2186–2199, doi:10.3762/bjoc.10.226

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  • wanted to use direct functionalization either via C–H activation or cross dehydrogenative coupling for C–C-bond-forming reactions avoiding the use of two prefunctionalized building blocks. Naturally, C–N-bond formation should proceed via BuchwaldHartwig coupling. The target molecules can be considered
  • -diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts. Keywords: Buchwald
  • Hartwig coupling; C–C coupling; C–H functionalization; iron catalysis; regioselective arylation; Introduction 1,2,3,4-Tetrahydroisoquinolines (THIQs) are common substructures in natural products [1]. The structural motif of 1-(indol-3-yl)-THIQ is also found in compounds with biological activity, for
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Published 15 Sep 2014

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

  • Maja Kandziora and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

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  • prepared p-bromophenyl-substituted bicyclic 1,2-oxazine derivatives 12, 13, 15 and 16 provide options to perform cross-coupling reactions such as Buchwald/Hartwig, Heck, Hiyama, Kumada, Sonogashira or Stille couplings. In order to examine the conditions for Suzuki cross-couplings we subjected bicyclic
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Published 30 Jul 2014

Visible light mediated intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes

  • Theresa H. Nguyen,
  • Soumitra Maity and
  • Nan Zheng

Beilstein J. Org. Chem. 2014, 10, 975–980, doi:10.3762/bjoc.10.96

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  • -iodobenzene (19) and cycloproylamine, 2-bromo-N-cyclopropylaniline (20) was prepared in 75% yield via the BuchwaldHartwig amination [39][40]. The [3 + 2] annulation of 2-bromo-N-cyclopropylaniline (20) and phenylacetylene (2) was performed using the optimized catalyst system to provide cyclic allylic amine
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Published 29 Apr 2014

Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles

  • Zong Guan,
  • Jan C. Namyslo,
  • Martin H. H. Drafz,
  • Martin Nieger and
  • Andreas Schmidt

Beilstein J. Org. Chem. 2014, 10, 832–840, doi:10.3762/bjoc.10.79

Graphical Abstract
  • available by copper-catalyzed aryl couplings or BuchwaldHartwig reactions [22]. Pyrazol-3-ylidenes rearrange similarly to quinolines [17]. We report here on two unexpected rearrangements of indazol-3-ylidene, and trapping reactions of the N-heterocyclic carbene with rhodium. Results and Discussion On
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Published 10 Apr 2014

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

  • Marcus Baumann and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

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Published 30 Oct 2013

Camera-enabled techniques for organic synthesis

  • Steven V. Ley,
  • Richard J. Ingham,
  • Matthew O’Brien and
  • Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

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  • is visible with the aid of the video camera; (d) a still from the footage showing arcing observed as a bright flash of light. Video stills reprinted from [47], Copyright 2008, with permission from Elsevier. (a) BuchwaldHartwig coupling within a microchannel reactor. (b) Camera view of aggregate
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Published 31 May 2013

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

  • Torsten Dittrich,
  • Nils Hanekop,
  • Nacera Infed,
  • Lutz Schmitt and
  • Manfred Braun

Beilstein J. Org. Chem. 2012, 8, 1700–1704, doi:10.3762/bjoc.8.193

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  • precursor 2c was obtained by an N-arylation, as described in the literature.[21] A modified BuchwaldHartwig amination reaction using tri-tert-butylphosphane as a ligand at palladium [22] was applied in order to couple 4-methylphenyl bromide and 4-fluorophenyl bromide with Boc-protected aminopiperidines 17
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Published 05 Oct 2012

Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles

  • Anthony R. Martin,
  • Anthony Chartoire,
  • Alexandra M. Z. Slawin and
  • Steven P. Nolan

Beilstein J. Org. Chem. 2012, 8, 1637–1643, doi:10.3762/bjoc.8.187

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  • ) (Figure 1). Complexes 1 and 2 are commercially available and have proven to be highly efficient in Suzuki–Miyaura coupling and BuchwaldHartwig amination reactions [17][18][19][20]. We have also evaluated the recently reported [Pd(IPr*)(cin)Cl] (3), which has shown potency in Suzuki–Miyaura couplings [21
  • ] and BuchwaldHartwig N-arylations [22] even with challenging substrates. To complete this study and to examine the effect of bulky ligands about the metal centre, we have synthesised a new complex [Pd(IPr*Tol)(cin)Cl] (4), which is a IPr* congener. Results and Discussion The study begins with the
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Published 27 Sep 2012

Double N-arylation reaction of polyhalogenated 4,4’-bipyridines. Expedious synthesis of functionalized 2,7-diazacarbazoles

  • Mohamed Abboud,
  • Emmanuel Aubert and
  • Victor Mamane

Beilstein J. Org. Chem. 2012, 8, 253–258, doi:10.3762/bjoc.8.26

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  • system. Moderate to good yields were obtained in this site-selective BuchwaldHartwig double amination. The functionalization of these tricyclic derivatives was performed by using Pd-catalyzed cross-coupling reactions such as the Stille and Suzuki couplings. Two compounds were analyzed by X-ray
  • -diazacarbazole by using a palladium-catalyzed double N-arylation of 4,4’-dichloro-3,3’-bipyridine, itself obtained after a long reaction sequence [25][26][27]. In another patent, an intramolecular BuchwaldHartwig amination [28][29] was used to generate a 2,7-diazacarbazole derivative in low yield [30]. Recently
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Published 14 Feb 2012

Amines as key building blocks in Pd-assisted multicomponent processes

  • Didier Bouyssi,
  • Nuno Monteiro and
  • Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

Graphical Abstract
  • preparation of various 2,3-disubstituted indole derivatives 62 (Scheme 27). Amines as coupling partners through BuchwaldHartwig amination Other strategies used for the palladium-mediated three-component preparation of substituted indole derivatives involve an efficient BuchwaldHartwig amination as the key
  • coupling leading to a mono-alkynylated product, followed by an intermolecular BuchwaldHartwig amination and a subsequent intramolecular amination. This Pd-catalyzed tandem coupling reaction allows the preparation of a variety of 2-alkynylindoles 64 (Scheme 28). An elegant three-component process based on
  • transformations, including aza-Michael additions, hydroaminations of alkynes, BuchwaldHartwig aminations, and allylic aminations, thereby allowing the creation of several covalent bonds in a single operation. Imine derivatives are also of high synthetic value as they may act either as electrophilic or
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Published 10 Oct 2011

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated SNAr reaction

  • Charlotte Wiles and
  • Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

Graphical Abstract
  • ] (Figure 1). Installation of the diaryl ether can, however, be synthetically challenging, and this is illustrated by the wide number of techniques developed, which include Ullmann ether synthesis [6], Pummerer-type rearrangements [7], BuchwaldHartwig couplings [8], phenolic additions to amines [9
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Published 04 Oct 2011

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

  • Carolin Fischer and
  • Burkhard Koenig

Beilstein J. Org. Chem. 2011, 7, 59–74, doi:10.3762/bjoc.7.10

Graphical Abstract
  • applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed BuchwaldHartwig-type
  • -arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and BuchwaldHartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have
  • )TMEDA]2Cl2, omitting the base and working at room temperature [13][14]. Besides palladium and copper, nickel catalysis also allows the arylation of primary and secondary amines [15][16]. However, the three methods (Ullmann–Goldberg, BuchwaldHartwig and Chan–Lam) have become standard procedures for N
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Published 14 Jan 2011

Mitomycins syntheses: a recent update

  • Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

Graphical Abstract
  • insertion The laboratory of G.A. Sulikowski proposed a synthesis of 1,2-aziridinomitosenes [106][107] using as key transformations a BuchwaldHartwig cross-coupling [108][109][110] and a chemoselective intramolecular carbon-hydrogen metal-carbenoid insertion reaction (Scheme 39). The chiral pyrolidine 136
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Published 08 Jul 2009
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