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Search for "Suzuki–Miyaura" in Full Text gives 185 result(s) in Beilstein Journal of Organic Chemistry.

Clean and fast cross-coupling of aryl halides in one-pot

  • Valerica Pandarus,
  • Geneviève Gingras,
  • François Béland,
  • Rosaria Ciriminna and
  • Mario Pagliaro

Beilstein J. Org. Chem. 2014, 10, 897–901, doi:10.3762/bjoc.10.87

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  • Unsymmetrically coupled biaryls are synthesized in high yield starting from different aryl bromides and bis(pinacolato)diboron by carrying out the Miyaura borylation reaction followed by the SuzukiMiyaura reaction in the same reaction pot over 1–2 mol % SiliaCat DPP-Pd. The SiliaCat DPP-Pd catalyst is air-stable
  • and the method does not require the use of inert conditions. The use of non-toxic isopropanol or 2-butanol as reaction solvent further adds to the environmental benefits of this new green synthetic methodology. Keywords: borylation; SiliaCat; SuzukiMiyaura; cross-coupling; one-pot; Findings
  • Affording valued biaryls and heterobiaryls, namely ubiquitous chemical moieties in pharmaceuticals, natural products, photoactive species and many other functional molecules, the SuzukiMiyaura cross-coupling reaction is widely employed by the fine chemicals and pharmaceutical industries [1]. The reaction
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Published 22 Apr 2014

Columnar/herringbone dual crystal packing of pyrenylsumanene and its photophysical properties

  • Binod Babu Shrestha,
  • Shuhei Higashibayashi and
  • Hidehiro Sakurai

Beilstein J. Org. Chem. 2014, 10, 841–847, doi:10.3762/bjoc.10.80

Graphical Abstract
  • Pyrenylsumanene (1) was prepared from iodosumanene [8] and pyreneboronic acid in 84% yield through a SuzukiMiyaura cross-coupling reaction (Scheme 1). The preparation of iodosumanene was improved by using a catalytic amount of scandium (III)triflate (Sc(OTf)3) with 6,6’-diiodo-2,2’-dimethoxy-1,1’-binaphthol (DIH
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Published 11 Apr 2014

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

  • Michał Górny vel Górniak,
  • Anna Czernicka,
  • Piotr Młynarz,
  • Waldemar Balcerzak and
  • Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 741–745, doi:10.3762/bjoc.10.68

Graphical Abstract
  • % as the monophenyl ester. This library was enlarged by application of the SuzukiMiyaura approach with compounds 2e and 2k being chosen as substrates (Scheme 3) [23][24]. Despite the enormous number of data considering application of this reaction, according to the best of our knowledge, there is no
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Published 28 Mar 2014

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

  • Ju Hee Kim,
  • Su Jeong Choi and
  • In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

Graphical Abstract
  • . Since the use of a proper base in the SuzukiMiyaura reaction is an important factor to increase the yield of coupled product, we screened bases to get the optimized reaction conditions. When 2 was reacted with 1 equiv of phenylboronic acid in the presence of 5 mol % of Pd(OAc)2 and Cs2CO3 (2 equiv) in
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Published 14 Nov 2013

The chemistry of isoindole natural products

  • Klaus Speck and
  • Thomas Magauer

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

Graphical Abstract
  • following one-pot SuzukiMiyaura/aldol condensation of 134 with boronic acid 135 was carried out at 150 °C in a microwave reactor and gave aristolactam BII (115) in good yield. By variation of the coupling partners, Heo was able to efficiently synthesize a library of natural and non-natural analogues
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Published 10 Oct 2013

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

  • Mark C. Bagley,
  • Vincenzo Fusillo,
  • Robert L. Jenkins,
  • M. Caterina Lubinu and
  • Christopher Mason

Beilstein J. Org. Chem. 2013, 9, 1957–1968, doi:10.3762/bjoc.9.232

Graphical Abstract
  • an encapsulated palladium catalyst by Baxendale and Ley, et al. [25], the latter to process multigram quantities in a microwave-assisted SuzukiMiyaura coupling. A comparison on the use of palladium(0) nanoparticle catalysts on glass-polymer composite materials in batch and flow-through experiments
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Published 30 Sep 2013

Synthesis of enones, pyrazolines and pyrrolines with gem-difluoroalkyl side chains

  • Assaad Nasr El Dine,
  • Ali Khalaf,
  • Danielle Grée,
  • Olivier Tasseau,
  • Fares Fares,
  • Nada Jaber,
  • Philippe Lesot,
  • Ali Hachem and
  • René Grée

Beilstein J. Org. Chem. 2013, 9, 1943–1948, doi:10.3762/bjoc.9.230

Graphical Abstract
  • possibility of using these molecules as scaffolds for the preparation of focused chemical libraries. In order to explore this possibility we developed representative examples of Pd-catalyzed reactions starting from p-bromo derivatives 4e and 6e. The results are given in Scheme 7 for pyrazoline 4e. Suzuki
  • Miyaura coupling [35] gave biphenyl derivative 7e in 82% yield, while the Heck [36] and Sonogashira [37] reactions afforded also the desired targets 8e and 9e in 72% and 77% yield respectively. Similar results were obtained in Pd-mediated reactions starting from pyrroline 6e, as indicated in Scheme 8. The
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Published 26 Sep 2013

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

  • Willmen Youngsaye,
  • Cathy L. Hartland,
  • Barbara J. Morgan,
  • Amal Ting,
  • Partha P. Nag,
  • Benjamin Vincent,
  • Carrie A. Mosher,
  • Joshua A. Bittker,
  • Sivaraman Dandapani,
  • Michelle Palmer,
  • Luke Whitesell,
  • Susan Lindquist,
  • Stuart L. Schreiber and
  • Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

Graphical Abstract
  • Two different routes were adopted to access the various functionalized indazoles required to evaluate the SAR associated with hit compound 1 (Scheme 1). The robust SuzukiMiyaura reaction was selected for the preparation of analogues bearing substituents around the central indazole core. This approach
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Published 26 Jul 2013

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

  • Helga Seyler,
  • Jegadesan Subbiah,
  • David J. Jones,
  • Andrew B. Holmes and
  • Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

Graphical Abstract
  • SuzukiMiyaura and Stille coupling [12]. In this study, the continuous-flow synthesis of P3HT is examined. Distinct from a recent report of P3HT synthesis in a droplet-based microreactor [20], development of the flow synthesis is described in detail and controlled polymerization of P3HT, both in terms of
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Published 25 Jul 2013

Incorporation of perfluorohexyl-functionalised thiophenes into oligofluorene-truxenes: synthesis and physical properties

  • Neil Thomson,
  • Alexander L. Kanibolotsky,
  • Joseph Cameron,
  • Tell Tuttle,
  • Neil J. Findlay and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2013, 9, 1243–1251, doi:10.3762/bjoc.9.141

Graphical Abstract
  • -iodo-4-perfluorohexylthiophene, which was separated by column chromatography. Compound 4 then underwent SuzukiMiyaura coupling with compound 5, which was synthesised according to our previously published method [17], and the product obtained, 6, was deprotected by bromination to give compound 7 and
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Published 27 Jun 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

Graphical Abstract
  • reported the application of the synthetically powerful SuzukiMiyaura reaction within aqueous microdroplets buffered by catalytically active fluorous interfaces [45]. Images of the flow channels captured by a high-speed camera provided preliminary kinetic data by allowing the precipitation of the solid
  • setup that might not otherwise be available. SuzukiMiyaura reaction performed within a microfluidic system. The product is observed by high-speed microscope photography, which shows a precipitate forming within the microdroplets. Friedel–Crafts reactions performed by using solid-acid catalysis at high
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Published 31 May 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

Graphical Abstract
  • hydride-AIBN initiated radical cyclization [33][34]. In 2005, Player and co-workers reported a tandem Heck/SuzukiMiyaura coupling process for the synthesis of (E)-3,3-(diaryl)oxindoles [35][36][37]. Recently, alkenylation of indolin-2-ones has been developed by palladium-catalyzed aromatic C–H activation
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Published 25 Apr 2013

Synthesis and structure of trans-bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride and diacetate. Suzuki–Miyaura coupling of polybromoarenes with high catalytic turnover efficiencies

  • Jeelani Basha Shaik,
  • Venkatachalam Ramkumar,
  • Babu Varghese and
  • Sethuraman Sankararaman

Beilstein J. Org. Chem. 2013, 9, 698–704, doi:10.3762/bjoc.9.79

Graphical Abstract
  • Abstract trans-Bis(1,4-dimesityl-3-methyl-1,2,3-triazol-5-ylidene)palladium(II) dichloride has been shown to be an excellent catalyst for the multiple SuzukiMiyaura coupling reactions of polybromoarenes to the corresponding fully substituted polyarylarenes. The reactions proceeded in excellent yields and
  • structures of the chloro (1) as well as the corresponding acetato (2) complexes are also reported and compared with the corresponding complexes of 1,4-diphenyl-3-methyl-1,2,3-triazol-5-ylidene as the ligand. Keywords: C–C coupling; N-heterocyclic carbene; palladium; SuzukiMiyaura coupling; 1,2,3
  • reactions one often encounters the formation of partially coupled products and incomplete reactions leading to problematic separation of pure fully substituted compounds. Herein we report very clean multiple SuzukiMiyaura coupling of polybromoarenes. In every case reported herein the final product, namely
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Published 10 Apr 2013

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

Graphical Abstract
  • ) (Figure 1). Complexes 1 and 2 are commercially available and have proven to be highly efficient in SuzukiMiyaura coupling and Buchwald–Hartwig amination reactions [17][18][19][20]. We have also evaluated the recently reported [Pd(IPr*)(cin)Cl] (3), which has shown potency in SuzukiMiyaura couplings [21
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Published 27 Sep 2012

Sonogashira–Hagihara reactions of halogenated glycals

  • Dennis C. Koester and
  • Daniel B. Werz

Beilstein J. Org. Chem. 2012, 8, 675–682, doi:10.3762/bjoc.8.75

Graphical Abstract
  • SuzukiMiyaura coupling with iodoglucals 6 to yield aliphatic C-glycosides [19]. This method impressively demonstrates the power of the SuzukiMiyaura coupling in the formation of C(sp2)–C(sp3) bonds for the preparation of carbohydrate mimetics. Friesen and co-workers reported on a synthesis of aryl-C
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Published 02 May 2012

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

  • Jiří Kulhánek and
  • Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

Graphical Abstract
  • chromophores 95–100 (Figure 18; [112]). The synthesis of this series of chromophores involved two-fold SuzukiMiyaura and Sonogashira cross-coupling reactions on dibromoolefin 94 (for X-ray structure see [113]). This compound proved to be a very useful, fully planar precursor for the construction of a
  • –111 (Figure 19; [20]). In contrast to a typical synthetic approach to diimidazoles as shown in Scheme 1, we used 4,5-dicyanoimidazole derivatives 1–3 (Scheme 2) and modern direct arylation, SuzukiMiyaura, Sonogashira, and Heck reactions to construct molecules 101–111. These chromophores possess two
  • on alkoxysilanes [105][106]. This new material is to be applied as an electro-optic modulator. Our synthetic efforts in the field of 4,5-dicyanoimidazole-derived chromophores began with the initial set of push–pull molecules 88–93 (Figure 16; [30]). Chromophores 88–93 were synthesized by Suzuki
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Published 05 Jan 2012

Sexithiophenes as efficient luminescence quenchers of quantum dots

  • Christopher R. Mason,
  • Yang Li,
  • Paul O’Brien,
  • Neil J. Findlay and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

Graphical Abstract
  • of 7a and 7b in modest yields (40% and 20%, respectively). Sexithiophenes 1a and 1b were subsequently isolated following SuzukiMiyaura coupling with 4-(dimethylamino)phenylboronic acid (1a, 28%; 1b, 44%). As a comparison, nonfunctionalised sexithiophenes 2a and 2b were also synthesised in order to
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Published 22 Dec 2011

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

Graphical Abstract
  • direct (hetero)arylation of (hetero)arenes is an attractive alternative to traditional Kumada, Stille, Negishi and SuzukiMiyaura cross-coupling reactions, notably as it avoids the prior preparation and isolation of (hetero)arylmetals. Developments of this methodology in the oxazole series are reviewed
  • , aminomethylation, sulfuration, oxygenation). However, aryllithiums can rarely be directly involved in transition-metal-catalyzed cross-coupling reactions and are usually transformed into organometallic fragments suitable for efficient Negishi, Stille, SuzukiMiyaura, and Hiyama cross-coupling reactions [1][2
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Published 29 Nov 2011

A novel and facile synthesis of 3-(2-benzofuroyl)- and 3,6-bis(2-benzofuroyl)carbazole derivatives

  • Wentao Gao,
  • Meiru Zheng and
  • Yang Li

Beilstein J. Org. Chem. 2011, 7, 1533–1540, doi:10.3762/bjoc.7.180

Graphical Abstract
  • presence of fluorine, chlorine, or bromine substituents (entries 6–11) is not problematic, thereby providing a potential handle for further functionalization (eg., Heck and SuzukiMiyaura reactions) of the corresponding products 3f–k. In the cases of entries 9–11, the tert-butyl-substituted products 3i–k
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Published 17 Nov 2011

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

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  • stereoselectivity. A four-component reaction was further developed through an in situ post C–B arylation by adding a second aryl iodide, with Cs2CO3 and water, to the newly formed alkenylboronate 78. The subsequent SuzukiMiyaura coupling led to the formation of 2,3-diarylated amines 79 and the best results were
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Published 10 Oct 2011

Bromine–lithium exchange: An efficient tool in the modular construction of biaryl ligands

  • Laurence Bonnafoux,
  • Frédéric R. Leroux and
  • Françoise Colobert

Beilstein J. Org. Chem. 2011, 7, 1278–1287, doi:10.3762/bjoc.7.148

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  • -methylation with iodomethane in acetone. 2,2'-Dibromo-6-methoxybiphenyl (1d) was finally obtained in a very good global yield of 68% in 3 steps. Finally, we proposed to introduce the phenyl ring (1f, 95%) by a regioselective SuzukiMiyaura coupling via the iodo derivative 1e, the latter being obtained in 83
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Published 14 Sep 2011

Directed aromatic functionalization

  • Victor Snieckus

Beilstein J. Org. Chem. 2011, 7, 1215–1218, doi:10.3762/bjoc.7.141

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  • insertion, the gates of the synthetic arena were spectacularly opened to the 2010 Nobel Prize chemistry and the general theme of transition metal-catalyzed reactions. Thus, the named reactions of Kumada–Corriu, Negishi, SuzukiMiyaura, Stille and, most recently, Hiyama have all given new insights into how
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Published 06 Sep 2011

Scaling up of continuous-flow, microwave-assisted, organic reactions by varying the size of Pd-functionalized catalytic monoliths

  • Ping He,
  • Stephen J. Haswell,
  • Paul D. I. Fletcher,
  • Stephen M. Kelly and
  • Andrew Mansfield

Beilstein J. Org. Chem. 2011, 7, 1150–1157, doi:10.3762/bjoc.7.133

Graphical Abstract
  • been developed to perform SuzukiMiyaura reactions under a microwave heating regime, in which the volumetric throughput of a Pd-supported silica monolith can be used to increase the quantity of the product without changing the optimal operating conditions. Two silica monoliths (both 3 cm long), with
  • , respectively. Under optimal reaction conditions the quantity of product could be increased from 31 mg per hour to 340 mg per hour simply by changing the volumetric capacity of the monolith. Keywords: continuous flow; microwave heating; monolith; scaling-up; SuzukiMiyaura reaction; Introduction Interest in
  • heating. The practicality of this approach will be demonstrated using SuzukiMiyaura reactions in which the Pd-supported silica-monolith catalysts exhibit excellent activities and the doubling of the monolith diameter, thus operating at four times the volumetric flow rate, increases product output without
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Published 23 Aug 2011

Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis

  • Lian-jun Liu,
  • Feijun Wang,
  • Wenfeng Wang,
  • Mei-xin Zhao and
  • Min Shi

Beilstein J. Org. Chem. 2011, 7, 555–564, doi:10.3762/bjoc.7.64

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  • '-biphenyl backbone have been prepared from chiral 6,6'-dimethoxybiphenyl-2,2'-diamine. The complexes were characterized by X-ray crystal structure diffraction. The Pd(II) complex showed good catalytic activities in the SuzukiMiyaura and Heck–Mizoroki coupling reactions, and the (S)-Au(I) complexes also
  • showed good catalytic activities in the asymmetric intramolecular hydroamination reaction to give the corresponding product in moderate ee. Keywords: chiral mono(N-heterocyclic carbene) complex; Heck–Mizoroki reaction; hydroamination; SuzukiMiyaura reaction; Introduction N-heterocyclic carbene (NHC
  • coupling reactions and a Au-catalyzed asymmetric reaction, respectively. SuzukiMiyaura and Heck–Mizoroki coupling reactions catalyzed by NHC–Pd(II) complex The Pd-catalyzed coupling reaction is one of the most powerful methods for the formation of carbon–carbon bonds in organic synthesis [60][61][62][63
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Published 04 May 2011
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  • Qingwei Du Yiqun Li Department of Chemistry, Jinan University, 510632 Guangzhou, China 10.3762/bjoc.7.48 Abstract A diphenylphosphinite cellulose palladium complex (Cell–OPPh2–Pd0) was found to be a highly efficient heterogeneous catalyst for the SuzukiMiyaura reaction. The products were
  • catalyst; SuzukiMiyaura reaction; Introduction The formation of Csp2–Csp2 bonds has long remained a difficult task until the development of the SuzukiMiyaura palladium-catalyzed reaction [1][2][3]. The palladium-catalyzed Suzuki cross-coupling reaction of aryl halides with arylboronic acids is one of
  • . Moreover, it showed excellent catalytic activity in the SuzukiMiyaura coupling reaction of various aryl haildes bearing electron-withdrawing and/or electron-donating groups. Results and Discussion Synthesis and characterization of Cell–OPPh2 and Cell–OPPh2–Pd0 It is well known that nanopalladium shows
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Published 30 Mar 2011
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