Search results

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

One-pot sequential synthesis of tetrasubstituted thiophenes via sulfur ylide-like intermediates

  • Jun Ki Kim,
  • Hwan Jung Lim,
  • Kyung Chae Jeong and
  • Seong Jun Park

Beilstein J. Org. Chem. 2018, 14, 243–252, doi:10.3762/bjoc.14.16

Graphical Abstract
  • methods [44][45][46][47][48][49]. In general, Pd-catalyzed SuzukiMiyaura cross-coupling reactions are the most popular synthetic strategy for aryl–aryl bond-forming reactions [50][51][52]. However, it has been reported that the Suzuki cross-coupling of nitrogen- and sulfur-containing heterocycles is more
PDF
Album
Supp Info
Full Research Paper
Published 26 Jan 2018

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

  • Baris Temelli and
  • Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

Graphical Abstract
  • -porphyrin, β-corrole-linked hybrid structure described a SuzukiMiyaura cross-coupling reaction between a β-borylated corrole and meso-bromoporphyrins (Scheme 1D) [37]. Recently, we have successfully synthesized meso–meso and β-meso-linked imine-bridged porphyrin–corrole conjugates and investigated
PDF
Album
Supp Info
Full Research Paper
Published 22 Jan 2018

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

  • Mattias Bood,
  • Sangamesh Sarangamath,
  • Moa S. Wranne,
  • Morten Grøtli and
  • L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

Graphical Abstract
  • a more straightforward and versatile synthetic route. The Stille coupling was changed to a SuzukiMiyaura coupling and the cyclization was performed directly starting from the free aniline nitrogen, as we found that Boc protection was required only for cyclization when using DBU and DABCO. To faster
PDF
Album
Review
Published 10 Jan 2018

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

  • Jan Podlesný,
  • Lenka Dokládalová,
  • Oldřich Pytela,
  • Adam Urbanec,
  • Milan Klikar,
  • Numan Almonasy,
  • Tomáš Mikysek,
  • Jaroslav Jedryka,
  • Iwan V. Kityk and
  • Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

Graphical Abstract
  • 7 using a larger excess of NBS resulted in its decomposition. According to the current literature reports [18][19][27], DPP derivative 8 undergoes smooth cross-coupling reactions. Hence, we have utilized twofold SuzukiMiyaura and Migita–Stille reactions leading to chromophores 1a–3a and 4a
  • , respectively. Commercially available 4-(N,N-dimethylamino)phenylboronic, 4-methoxyphenylboronic, and 2-thienylboronic acids completed with tributyl(5-methoxythiophen-2-yl)stannane, prepared from 2-methoxythiophene [33], were used. Chromophore 4a was also attempted by SuzukiMiyaura reaction using the
  • in modular way prepared by SuzukiMiyaura, Migita–Stille, and Sonogashira cross-coupling reactions. The chromophores differ in the π-system extension as well as in the peripheral substitution. The thermal stability of 1–5 is mostly affected by the presence of acetylene linkers, 1,4-phenylene and 2,5
PDF
Album
Supp Info
Full Research Paper
Published 08 Nov 2017

Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

  • Tao Wang,
  • Yan-Chao Zhao,
  • Li-Min Zhang,
  • Yi Cui,
  • Chang-Shan Zhang and
  • Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

Graphical Abstract
  • organic polymers (POPs) have been reported via Sonogashira–Hagihara coupling reaction [16], SuzukiMiyaura chemistry [17], Yamato reaction [18], and self condensation of aromatic nitriles[19]. Although these methods can be used to construct POPs with high specific surface area values, these reactions are
PDF
Album
Supp Info
Full Research Paper
Published 12 Oct 2017

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

  • Layal Hariss,
  • Kamal Bou Hadir,
  • Mirvat El-Masri,
  • Thierry Roisnel,
  • René Grée and
  • Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

Graphical Abstract
  • as an attractive precursor to increase the molecular diversity around this scaffold. In order to explore this possibility, we performed two SuzukiMiyaura reactions, as representative examples of Pd-catalyzed coupling processes (Table 3). They gave the target molecules 8 and 9 in 46% and 53% yields
PDF
Album
Supp Info
Full Research Paper
Published 10 Oct 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

Graphical Abstract
  • of their low reactivity. Recently, Li and Su with co-workers have developed a liquid-assisted grinding (LAG) method for the SuzukiMiyaura coupling between aryl chlorides and boronic acids to synthesize the biaryls in nearly quantitative yield. Under optimized conditions 2 mol % Pd(OAc)2 and 4 mol
  • ]. Mechanochemical Suzuki reaction [56]. Mechanochemical SuzukiMiyaura coupling by LAG [57]. Mechanochemical Heck reaction [59]. a) Sonogashira coupling under milling conditions. b) The representative example of a double Sonogashira reaction of p-iodoacetophenone with 1,4-bis-ethynyl benzene. Copper-catalyzed CDC
PDF
Album
Review
Published 11 Sep 2017

An efficient Pd–NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki–Heck reactions in water

  • Nan Sun,
  • Meng Chen,
  • Liqun Jin,
  • Wei Zhao,
  • Baoxiang Hu,
  • Zhenlu Shen and
  • Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 1735–1744, doi:10.3762/bjoc.13.168

Graphical Abstract
  • contributed to SuzukiMiyaura reactions and only a very few examples were reported for Mizoroki–Heck reactions [45][51][53][57]. Previous research by Rösch and other groups disclosed that introducing a hemilable donor group (such as N, O, S etc.) on the NHC rings was favorable for the palladium-catalyzed
PDF
Album
Supp Info
Full Research Paper
Published 21 Aug 2017

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

  • Carolina S. García,
  • Paula M. Uberman and
  • Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

Graphical Abstract
  • H2PdCl4 in the presence of poly(N-vinylpirrolidone) (PVP) [46][47]. These Pd NPs exhibited highly efficient catalytic activity in SuzukiMiyaura coupling reactions [46][47] and nitroaromatic hydrogenations [48] in aqueous medium. Outstanding performance of these PVP-Pd NPs in the coupling reaction was
  • , precipitation or organic extraction eventually lead to a dramatic drop of the catalytic activity. As a result of this, and in order to perform the reuse experiment, repeated runs on the same batch were performed; reusing the reaction mixture with the PVP-Pd nanocatalyst. By this procedure in both, Suzuki
  • Miyaura coupling reaction [46] and nitroaromatic hydrogenation [48], the PVP-Pd NPs catalytic system exhibited high catalytic activity after five cycles. In the Heck–Mizoroki coupling reaction under MW irradiation, once the reaction was completed, a new batch of reagents was added to the reaction tube and
PDF
Album
Supp Info
Full Research Paper
Published 18 Aug 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Graphical Abstract
PDF
Album
Review
Published 11 Aug 2017

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

  • Alexei N. Kiselev,
  • Olga K. Grigorova,
  • Alexei D. Averin,
  • Sergei A. Syrbu,
  • Oskar I. Koifman and
  • Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

Graphical Abstract
  • ][11], SuzukiMiyaura [12][13][14][15] and Stille couplings [16][17][18][19][20][21][22] were successfully applied for this purpose. Direct arylation and alkenylation are modern approaches for the formation of C–C bonds, and the application of these methodologies to porphyrins was widely studied by
PDF
Album
Supp Info
Full Research Paper
Published 03 Aug 2017

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

  • Kohei Yamada,
  • Naoto Kamimura and
  • Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

Graphical Abstract
  • one-pot oxazole synthesis/SuzukiMiyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed SuzukiMiyaura coupling with boronic acids provided the corresponding
  • 2,4,5-trisubstituted oxazoles in good yields. Keywords: one-pot oxazole synthesis; SuzukiMiyaura coupling; triazine; 5-(triazinyloxy)oxazole; trisubstituted oxazole; Introduction Oxazoles are found in numerous natural products and are used as a broad range of artificial compounds [1][2]. In
  • , Jin and co-workers reported that Ni-catalyzed SuzukiMiyaura coupling between triazinyloxybenzene and arylboronic acids affords the corresponding biaryl compounds [24][25][26][27][28][29][30][31][32][33]. In this context, we envisioned application of this SuzukiMiyaura coupling to a 5-(triazinyloxy
PDF
Album
Supp Info
Full Research Paper
Published 27 Jul 2017

Synthesis of the heterocyclic core of the D-series GE2270

  • Christophe Berini,
  • Thibaut Martin,
  • Pierrik Lassalas,
  • Francis Marsais,
  • Christine Baudequin and
  • Christophe Hoarau

Beilstein J. Org. Chem. 2017, 13, 1407–1412, doi:10.3762/bjoc.13.137

Graphical Abstract
  • heterocyclic core of the D-series thiopeptide antibiotic GE2270 was prepared. The synthetic strategy that combines direct C–H arylation, Borylation SuzukiMiyaura cross-coupling (BSC) and Hantzsch thiazole synthesis methods proved to be highly effective regarding the fair 22% yield over 7 synthetic steps from
PDF
Album
Supp Info
Full Research Paper
Published 17 Jul 2017

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

  • Roman A. Irgashev,
  • Nikita A. Kazin,
  • Gennady L. Rusinov and
  • Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

Graphical Abstract
  • performed by using the SuzukiMiyaura cross-coupling reaction with phenylboronic acid under Pd catalysis (Scheme 5). The location of the formyl group and bromine atoms in ICZ derivatives 12 and 13 has been established by X-ray crystallography analysis, performed for single crystals of 12b and 13b (Figure 5
PDF
Album
Supp Info
Full Research Paper
Published 14 Jul 2017

Total synthesis of elansolids B1 and B2

  • Liang-Liang Wang and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2017, 13, 1280–1287, doi:10.3762/bjoc.13.124

Graphical Abstract
  • first synthesis of elansolid B2 (3). The key for improvement was to abandon the two Sonogashira reactions along with the syn-reductions of the two alkynes. Instead, we planned to utilize the SuzukiMiyaura and the Stille reactions and two Z-configured vinyl iodides to assemble the (Z,E,Z)-triene unit
  • . Results and Discussion The improved synthesis utilizes the SuzukiMiyaura cross-coupling reaction to merge the western fragment derived from ketone 9 with the newly designed eastern building block 13. This fragment was obtained in very good yield from vinyl iodide 12 [9] by a Stille protocol using doubly
  • iodide 17 after O-acylation, iodination of the terminal alkyne and finally diimide-mediated syn-reduction [11]. Next, DDQ-mediated removal of the PMB protecting group yielded vinyl iodide 18. The synthesis of both fragments 13 and 18 set the stage for the SuzukiMiyaura coupling which delivered the
PDF
Album
Supp Info
Full Research Paper
Published 28 Jun 2017

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

  • Chinmay A. Shukla and
  • Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

Graphical Abstract
  • kinetics parameters of a series-parallel substitution reaction [38]. Reizman et al. have studied SuzukiMiyaura cross-coupling optimization using a DoE-based algorithm and feedback system [45]. The authors studied both continuous and discrete variables for optimization. Recently Fitzpatrick and Ley have
PDF
Album
Review
Published 19 May 2017

Synthesis of tetrasubstituted pyrazoles containing pyridinyl substituents

  • Josef Jansa,
  • Ramona Schmidt,
  • Ashenafi Damtew Mamuye,
  • Laura Castoldi,
  • Alexander Roller,
  • Vittorio Pace and
  • Wolfgang Holzer

Beilstein J. Org. Chem. 2017, 13, 895–902, doi:10.3762/bjoc.13.90

Graphical Abstract
  • been also observed in the course of related Pd-catalyzed cross-coupling reactions, such as, for instance, in SuzukiMiyaura reactions [38]. In contrast, the corresponding 2-pyridinyl or 2-thienyl organozinc congeners gave much better results with nearly no homocoupling side reactions and only few
PDF
Album
Supp Info
Full Research Paper
Published 12 May 2017

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

  • Flavio Fanelli,
  • Giovanna Parisi,
  • Leonardo Degennaro and
  • Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

Graphical Abstract
  • polyfunctionalized biaryls, using a flow microreactor, has been recently reported by Yoshida [54]. Using the integrated microflow system reported in Scheme 8, arylboronic esters were prepared by a lithiation/borylation sequence, and used in a SuzukiMiyaura coupling in a monolithic reactor. A remarkable aspect of
  • the process was the use of an integrated supported monolithic Pd(0) catalyst that allowed to perform cross-coupling reactions in continuous flow mode (Scheme 8). This integrated microflow system allow to handle the borylation of aryl halides (Ar1X), and the subsequent SuzukiMiyaura coupling using
  • different aryl halide (Ar2X). Without requiring the protection of sensitive functionalities, running the flow system using a residence time (tR) of about 4.7 min at a temperature above 100 °C, high yields of coupling products were obtained. Noteworthy, the SuzukiMiyaura coupling did not require the use of
PDF
Album
Review
Published 14 Mar 2017

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

  • Michal Medvecký,
  • Igor Linder,
  • Luise Schefzig,
  • Hans-Ulrich Reissig and
  • Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

Graphical Abstract
  • investigated the synthesis of 4-halogen- and 4,5-bis(halogen)-substituted 6H-1,2-oxazines by halogenation of 6H-1,2-oxazines and subsequent palladium-catalyzed coupling reactions such as Sonogashira or SuzukiMiyaura reactions [24] leading to aryl- and alkynyl-functionalized products. The synthetic potential
  • , since it is well documented that in related cross-coupling reactions of 16 exclusively the Z-isomers are formed [40]. The 5-iodo-1,2-oxazines syn-4a,b reacted smoothly under standard conditions of SuzukiMiyaura coupling reactions [45] with vinylboronic acid 18 and 3-methoxyphenylboronic acid 20 to
  • reactions of 1,2-oxazine syn-4a leading to 5-alkenyl-substituted 1,2-oxazines syn-13, syn-14 and to dehydroamino acid syn-17. SuzukiMiyaura reactions of 1,2-oxazines syn-4a, syn-4b and anti-4d leading to 5-styryl-substituted 1,2-oxazine syn-19 and 5-aryl-substituted 1,2-oxazines syn-21, syn-22 and anti-24
PDF
Album
Supp Info
Full Research Paper
Published 29 Dec 2016

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

  • Paul B. Geraghty,
  • Calvin Lee,
  • Jegadesan Subbiah,
  • Wallace W. H. Wong,
  • James L. Banal,
  • Mohammed A. Jameel,
  • Trevor A. Smith and
  • David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

Graphical Abstract
  • π-bridges by simple SuzukiMiyaura cross-coupling reactions could be completed. Starting with commercially available 5-bromothiophene-2-carboxaldehyde and then reaction with 3a–c to generate the required bithiophenes, then terthiophenes, while further catenation with 3b resulted in synthesis of the
  • analytically pure material isolated by filtration in excellent yields >90%, Scheme 4. This simplified purification is in direct contrast with reported procedures for the bis-iodinated or bis-stannylated analogues [20][21]. A simple SuzukiMiyaura cross coupling of 5, 7, 9 or 11 with 13 gave the required BXx
PDF
Album
Supp Info
Full Research Paper
Published 02 Nov 2016

Elongated and substituted triazine-based tricarboxylic acid linkers for MOFs

  • Arne Klinkebiel,
  • Ole Beyer,
  • Barbara Malawko and
  • Ulrich Lüning

Beilstein J. Org. Chem. 2016, 12, 2267–2273, doi:10.3762/bjoc.12.219

Graphical Abstract
  • the SuzukiMiyaura coupling [11]. A retrosynthetic analysis (Figure 3) of extended mono-functionalized triazinetricarboxylic acids 2 calls for tris(4-bromoaryl)-1,3,5-triazines 3 and boronic acids 4 with an additional carboxylic acid functionality. The respective methyl carboxylate of boronic acid 4
  • ) MeOH/H2SO4, MeOH, 16 h, reflux, 94%, c) Me2SO4, K2CO3, acetone, 3 h, reflux, quant., d) MeI, K2CO3, DMF, 16 h, room temperature, 83%, e) NaOH, H2O, MeOH, 6 h, room temperature, 66%, f) SOCl2, DMF (cat.), 2 h, reflux, not isolated. Triple SuzukiMiyaura coupling between tribromotriazines 3 and boronic
PDF
Album
Supp Info
Full Research Paper
Published 27 Oct 2016

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

  • Maddali L. N. Rao,
  • Jalindar B. Talode and
  • Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

Graphical Abstract
  • ambipolar materials (CZBDF, Figure 1c) [16]. To note, synthetic functionalization under transition-metal-catalyzed conditions allows the preparation of multi-substituted benzofurans in a facile manner [23][24][25][26][27][28]. Langer et al. reported the site-selective SuzukiMiyaura reaction of 2,3
PDF
Album
Supp Info
Full Research Paper
Published 22 Sep 2016

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

  • Kirsty L. Wilson,
  • Alan R. Kennedy,
  • Jane Murray,
  • Ben Greatrex,
  • Craig Jamieson and
  • Allan J. B. Watson

Beilstein J. Org. Chem. 2016, 12, 2005–2011, doi:10.3762/bjoc.12.187

Graphical Abstract
  • . Keywords: Cacchi annulation; cross-coupling; heterocycles; Sonogashira; sustainable solvent; Introduction The Sonogashira reaction [1][2] (Scheme 1) is a robust and broadly applicable Pd-catalysed bond-forming process that, alongside the SuzukiMiyaura reaction [3], has steadily become an indispensible
  • fundamental reactions that typically employ DMF [31][32]. The replacement of solvents with regulatory issues with bio-derived alternatives has provided a series of advances within the cross-coupling arena [33], allowing efficient C–C bond formation via cornerstone Pd-based methods including SuzukiMiyaura [34
  • -used organic transformations. For example, the majority of many other standard cross-coupling processes employ inorganic or organic bases and heat (e.g., SuzukiMiyaura, Heck). Accordingly, Cyrene may be projected to be incompatible with standard conditions for these reactions and its use would
PDF
Album
Supp Info
Full Research Paper
Published 08 Sep 2016

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

  • Takashi Nishikata,
  • Alexander R. Abela,
  • Shenlin Huang and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

Graphical Abstract
  • ”), there was a noticeable drop in the extent of conversion. In addition, lower loadings of HBF4, silver salt, or the palladium catalyst also gave inferior results. In the case of C–H activation/SuzukiMiyaura coupling reactions, the commercially available, pre-formed cationic Pd(II) catalyst [Pd(MeCN)4
  • groups, as well as sterically hindered aromatic rings, all taking place at room temperature. SuzukiMiyaura-type C–H coupling reactions are typically more tolerant of electron-withdrawing groups (3d, 3f, 3k) and ortho-substitution (3g) on the aryl ring. On the other hand, the reaction with 4
  • SuzukiMiyaura coupling reactions were applicable to a broader substrate scope than the corresponding reaction with aryl iodides, although the latter protocol remains appealing for a variety of cross-coupling combinations due to both the convenience of aryl iodides as substrates, and the use of water as
PDF
Album
Supp Info
Full Research Paper
Published 20 May 2016

Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

  • Shaojin Gu,
  • Jiehao Du,
  • Jingjing Huang,
  • Huan Xia,
  • Ling Yang,
  • Weilin Xu and
  • Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

Graphical Abstract
  • and platinum complexes containing 1,2,3-triazole-tethered NHC ligands. The obtained palladium complexes displayed high activity in aqueous SuzukiMiyaura cross-coupling reactions. We are interested in the synthesis and use of functionalized NHC ligands [20][28][29][30][31]. Herein, the synthesis
PDF
Album
Supp Info
Full Research Paper
Published 03 May 2016
Other Beilstein-Institut Open Science Activities