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Search for "Suzuki" in Full Text gives 349 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

  • Vitor A. S. Almodovar and
  • Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

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  • -di(het)aryl groups via Suzuki–Miyaura [26][27][28] or Sonogashira [29][30][31] reactions. In this study, we report a straightforward method to obtain a diverse array of N-substituted DPP derivatives through a two-step process. Firstly, the N-alkylation of Pigment Red 254 (DPP 1) is achieved using
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Published 08 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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  • , obtaining an enzyme-metal biohybrid catalyst [22]. The authors tested it in a one-pot GBB reaction–Suzuki coupling, employing 5-bromo-2-aminopyridine (20), benzaldehyde (2), tert-butyl isocyanide (5) and phenylboronic acid (21). Compound 22 was obtained in 87% yield by performing the GBB reaction at room
  • Suzuki–Miyaura reaction and then subjected the adduct 52 to a GBB reaction with various aldehydes and isocyanides (Scheme 20) [53]. Focusing on the GBB part, the authors tested both Lewis acids (Sc(OTf)3 or Yb(OTf)3) and Brønsted acids (NH4Cl or AcOH) and found that the best results could be obtained
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Published 01 Aug 2024

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

  • Ryo Tanifuji and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

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  • Suzuki–Miyaura coupling with boronic ester 53 and O-acetylation furnished 54. The dienophile component, morachalcone A (44), was synthesized from phenol 55 in four steps including O-prenylation and subsequent Claisen rearrangement, aldol condensation with 56, and deprotection. The key chemo-enzymatic
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Published 23 Jul 2024

Diameter-selective extraction of single-walled carbon nanotubes by interlocking with Cu-tethered square nanobrackets

  • Guoqing Cheng and
  • Naoki Komatsu

Beilstein J. Org. Chem. 2024, 20, 1298–1307, doi:10.3762/bjoc.20.113

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  • can calculate larger system (>500 atoms) containing transition metals more precisely [16][17]. Result and Discussion Synthesis of Cu-tethered square nanobrackets 1b A pyrene-based nanobracket 4b was synthesized via a one-pot Suzuki coupling followed by the formation of dipyrrin from the dialdehyde 3
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Published 05 Jun 2024

Introduction of peripheral nitrogen atoms to cyclo-meta-phenylenes

  • Koki Ikemoto and
  • Hiroyuki Isobe

Beilstein J. Org. Chem. 2024, 20, 1207–1212, doi:10.3762/bjoc.20.103

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  • achieved with one-pot Suzuki–Miyaura coupling to arrange phenylene rings and pyridinylene rings in an alternating fashion. Analyses with UV–vis spectroscopy showed changes in the photophysical properties with nitrogen doping, and X-ray crystallographic analyses experimentally revealed the presence of
  • were installed in an outward-radiated manner, which expands the structural diversity to exploit the chemistry at the periphery of [n]CMP (Figure 1b). Through the use of Suzuki–Miyaura coupling for macrocyclisation, pyridinyl and phenylene rings were assembled in an alternating fashion, which afforded
  • -doped [n]CMPs, 3a and 3b, were synthesized via one-pot Suzuki–Miyaura coupling [12] (Scheme 1). Previously, we synthesized [n]CMPs with inward-focused nitrogen dopants by using Suzuki–Miyaura coupling with Pd(PPh3)4 as the catalyst [13] and applied this method to outward-radiated congeners in this work
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Published 24 May 2024

Novel analogues of a nonnucleoside SARS-CoV-2 RdRp inhibitor as potential antivirotics

  • Luca Julianna Tóth,
  • Kateřina Krejčová,
  • Milan Dejmek,
  • Eva Žilecká,
  • Blanka Klepetářová,
  • Lenka Poštová Slavětínská,
  • Evžen Bouřa and
  • Radim Nencka

Beilstein J. Org. Chem. 2024, 20, 1029–1036, doi:10.3762/bjoc.20.91

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  • synthetic strategy leading to pyridones bearing different aryl substituents is described in Scheme 2. During the Suzuki–Miyaura cross-coupling reaction, which introduced the substituents in the C-5 position, the methyl ester protection of the amino acid moiety was also cleaved, leading directly to the final
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Published 06 May 2024

Spin and charge interactions between nanographene host and ferrocene

  • Akira Suzuki,
  • Yuya Miyake,
  • Ryoga Shibata and
  • Kazuyuki Takai

Beilstein J. Org. Chem. 2024, 20, 1011–1019, doi:10.3762/bjoc.20.89

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  • Akira Suzuki Yuya Miyake Ryoga Shibata Kazuyuki Takai Graduated School of Science and Engineering, Hosei University, Tokyo 184-8584, Japan Department of Chemical Science and Technology, Hosei University, Tokyo 184-8584, Japan 10.3762/bjoc.20.89 Abstract Ferrocene (FeCp2) was introduced as a non
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Published 02 May 2024

Carbonylative synthesis and functionalization of indoles

  • Alex De Salvo,
  • Raffaella Mancuso and
  • Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

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  • carbon monoxide insertion, and Suzuki–Miyaura coupling reaction, from 2-gem-dibromovinylaniline [12]. In the presence of Pd(PPh3)4 (5 mol %) as catalyst, 5 equivalents of base (K2CO3), an aryl- or heteroarylboronic ester (1.1 equivalents), CO (12 bar), in dioxane at 100 °C after 16 h the indole
  • /carbonylation/Suzuki coupling reaction for the synthesis of 2-aroylindoles and 2-heteroaroylindoles. Pd(0)-catalyzed single isonitrile insertion: synthesis of 1-(3-amino)-1H-indol-2-yl)-1-ketones. Pd(0)-catalyzed gas-free carbonylation of 2-alkynylanilines to 1-(1H-indol-1-yl)-2-arylethan-1-ones. Pd(II
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Published 30 Apr 2024

Synthesis and properties of 6-alkynyl-5-aryluracils

  • Ruben Manuel Figueira de Abreu,
  • Till Brockmann,
  • Alexander Villinger,
  • Peter Ehlers and
  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

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  • Abstract The development of a new and straightforward chemoselective method for the synthesis of uracil-based structures by combining Suzuki–Miyaura and Sonogashira–Hagihara cross-coupling is reported. The methodology was applied to synthesize a series of novel compounds. The tolerance of the combination
  • this work, we report a new chemoselective method for the synthesis of a series of hitherto unknown uracil-based compounds by combining Suzuki–Miyaura and Sonogashira–Hagihara cross-coupling [60][61]. The method is designed to be flexible and could also be used to synthesize other structural motifs
  • obtained. Compounds 3a–j were subsequently transformed to 5a–t by Suzuki–Miyaura cross-coupling. The bromination of 1 was performed by using Br2 (1 equiv), Ac2O (1.5 equiv), AcOH (25 °C, 1 h) and yielded the desired product in 52% [62]. With the starting material in hand, initial Sonogashira–Hagihara cross
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Published 22 Apr 2024

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

  • Jun Kikuchi,
  • Roi Nakajima and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

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  • Suzuki–Miyaura and Sonogashira couplings on 4aa or 4ba afforded the desired products 5 and 6 in 47% and 74% yields, respectively. In the former case, the C–Br bond on the pyrazole moiety remained intact, highlighting the superior leaving group ability of the BX group. Cu-catalyzed Ullmann coupling
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Published 22 Apr 2024

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

  • Jens Frackenpohl,
  • David M. Barber,
  • Guido Bojack,
  • Birgit Bollenbach-Wahl,
  • Ralf Braun,
  • Rahel Getachew,
  • Sabine Hohmann,
  • Kwang-Yoon Ko,
  • Karoline Kurowski,
  • Bernd Laber,
  • Rebecca L. Mattison,
  • Thomas Müller,
  • Anna M. Reingruber,
  • Dirk Schmutzler and
  • Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

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  • synthetic route, which enabled us to introduce a methyl substituent in this position. Likewise, methyl-substituted thiazolo[4,5-b]pyridines 5, 15a, and 15c were synthesized using an optimized Suzuki coupling and served together with compounds 12a–c as key intermediates to explore different reagents and
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Published 01 Mar 2024

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

  • Nahed Ketata,
  • Linhao Liu,
  • Ridha Ben Salem and
  • Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

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  • palladium-catalyzed direct intermolecular arylation, followed by a direct intramolecular arylation step. As the C–H bond activation of several benzene derivatives remains very challenging, the preparation of fluoranthenes from 1,8-dibromonaphthalene via Suzuki coupling followed by intramolecular C–H
  • contrast, only a few examples of fluoranthene backbone preparation by Pd-catalyzed C–H arylation have been reported. Some examples of the preparation of this skeleton by Suzuki coupling followed by intramolecular C–H coupling have been described [18][19][20][21][22][23][24]. In 2017, Metin, Türkmen and co
  • intermolecular Suzuki coupling with an intramolecular C–H arylation, it should be possible to access numerous fluoranthene derivatives from commercially available 1,8-dibromobenzene in a single manipulation (Scheme 1d). Here, we describe i) conditions enabling the annulative π-extension of 1,8-dibromonaphthalene
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Published 23 Feb 2024

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

  • Carlos R. Azpilcueta-Nicolas and
  • Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

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  • decarboxylative cross-coupling (DCC) of NHPI esters with organometallic reagents, resembling classic Kumada, Negishi, and Suzuki couplings, has been enabled by nickel (Ni), cobalt (Co), iron (Fe), and copper (Cu) catalysts [84][85][86][87][88][89][90][91] (Scheme 23A). The typical mechanism begins by
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Published 21 Feb 2024

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

  • Aissam Okba,
  • Pablo Simón Marqués,
  • Kyohei Matsuo,
  • Naoki Aratani,
  • Hiroko Yamada,
  • Gwénaël Rapenne and
  • Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

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  • corresponding boronic acid 9 and a Suzuki–Miyaura cross-coupling between 8 and 9 gave rise to dimer 10, followed by the oxidation of both acenaphthene units into 1,8-naphthalic anhydrides. Installation of the thiepine ring was achieved by a double nucleophilic aromatic substitution induced by sodium sulfide
  • corresponding bis(thiophenyl) thioether, which then underwent successive bromination and iodination to give intermediate 18. Next, a two-fold Suzuki–Miyaura cross-coupling occurring chemoselectively on the iodinated positions allowed the symmetric extension of the hydrocarbon scaffold, with the insertion of two
  • thiepine via a two-fold Suzuki–Miyaura cross-coupling with 1,2-phenylenediboronic pinacol ester. The resulting S-doped extended tribenzothiepine 21 proved stable under ambient conditions for several months and exhibited good solubility in common organic solvents, which is ascribed to the boat-shape
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Published 15 Feb 2024
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  • through scanning tunneling microscopy [85]. For TCBDs bearing unsubstituted anilino (p-H2NC6H4–) groups, their conversion into the p-iodophenyl derivatives via the Sandmeyer reaction and subsequent post-functionalization via the Suzuki and Sonogashira coupling reactions are achieved [86]. In the reaction
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Published 22 Jan 2024

Controlling the reactivity of La@C82 by reduction: reaction of the La@C82 anion with alkyl halide with high regioselectivity

  • Yutaka Maeda,
  • Saeka Akita,
  • Mitsuaki Suzuki,
  • Michio Yamada,
  • Takeshi Akasaka,
  • Kaoru Kobayashi and
  • Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

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  • Yutaka Maeda Saeka Akita Mitsuaki Suzuki Michio Yamada Takeshi Akasaka Kaoru Kobayashi Shigeru Nagase Department of Chemistry, Tokyo Gakugei University, Koganei, Tokyo 184-8501, Japan Department of Chemistry, Josai University, Sakado, Saitama 350-0295, Japan Tsukuba Advanced Research Alliance
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Published 11 Dec 2023

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application

  • Recep Isci and
  • Turan Ozturk

Beilstein J. Org. Chem. 2023, 19, 1849–1857, doi:10.3762/bjoc.19.137

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  • 4-bromo-N,N-diphenylaniline (5) with n-butyllithium at −78 °C and addition of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The Suzuki-coupling reaction of TT 4 with borolane 6 produced the intermediate 7 in 81% yield. The target D–π–A-type fluorophore, DMB-TT-TPA (8), was produced by
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Published 07 Dec 2023

Substituent-controlled construction of A4B2-hexaphyrins and A3B-porphyrins: a mechanistic evaluation

  • Seda Cinar,
  • Dilek Isik Tasgin and
  • Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

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  • mentioned by Osuka and Suzuki [13], besides the formation of A3B-porphyrins. On the other hand, electron-withdrawing but less bulky (4-trifluoromethylphenyl) groups on tripyrrane 5 led to predominant formation of the A3B-porphyrin even when it was reacted with mono-, di-, or penta-substituted aryl N
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Published 06 Dec 2023

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

  • Suangsiri Arunlimsawat,
  • Patteera Funchien,
  • Pongsakorn Chasing,
  • Atthapon Saenubol,
  • Taweesak Sudyoadsuk and
  • Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

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  • )diboron catalyzed by Pd(dpf)Cl2/KOAc. Finally, TPECNz was obtained as red solid in a reasonable yield by a Suzuki-type cross-coupling reaction between 3 and 4,9-dibromonaphtho[2,3-c][1,2,5]thiadiazole. The chemical structure and purity of compound 3 were verified by 1H NMR, 13C NMR, and high-resolution
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Published 03 Nov 2023

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

  • Jessica Villegas,
  • Bryce C. Ball,
  • Katelyn M. Shouse,
  • Caleb W. VanArragon,
  • Ashley N. Wasserman,
  • Hannah E. Bhakta,
  • Allen G. Oliver,
  • Danielle A. Orozco-Nunnelly and
  • Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

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  • complete decomposition. With the desired naphthylamines in hand, we were able to complete our synthesis of four chelerythrine variants as shown in Scheme 7. After N-formylation providing intermediates 11 and 12 in good yield, a three-step sequence was performed: Suzuki coupling of the aryl bromide with one
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Published 29 Sep 2023

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

  • Nadia Ledermann,
  • Alae-Eddine Moubsit and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

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  • electrophilic trapping of the intermediary indole anion with alkyl halides provides a concise one-pot synthesis of 3-iodoindoles. The latter are valuable substrates for Suzuki arylations, which are exemplified with the syntheses of four derivatives, some of them are blue emitters in solution and in the solid
  • alkynyl-substituted 3-iodoindole 6 as product in 42% isolated yield in the sense of a pseudo-five-component reaction (Scheme 3). Finally, the 3-iodoindole 5a and arylboronic acids 7 were employed in a standard Suzuki protocol with cesium carbonate as a base to give rise to the formation of 1,2,3
  • N-iodosuccinimide prior to N-alkylation to give substituted 3-iodoindoles in a concise consecutive four-component fashion in modest to good yields. These target compounds are versatile building blocks for instance for a Suzuki coupling to give 1-alkyl-2,3-diarylindoles that can be of particular
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Published 14 Sep 2023

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp3)–H to construct C–C bonds

  • Hui Yu and
  • Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

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  • Negishi reaction (Zn) [1], Stille reaction (Sn) [2], Kumada reaction (Mg) [3], and Suzuki reaction (Pd) [4] (Scheme 1a). However, these coupling reactions involve a metal exchange step that generates a considerable amount of reaction waste, such as metal salts, which are not environmentally friendly. To
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Published 06 Sep 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

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  • . Notably, carbonylative amidation of a borylated aryl bromide to 26d proceeded well, where a Pd-catalyzed carbonylative amidation reaction would be plagued by undesired Suzuki coupling. Several secondary cyclic and acyclic amines, as well as primary amines were successfully employed as amine coupling
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Published 28 Jul 2023

Construction of hexabenzocoronene-based chiral nanographenes

  • Ranran Li,
  • Di Wang,
  • Shengtao Li and
  • Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

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  • ]azepine and tetrabromothiophene-S,S-dioxide, followed by oxidative aromatization in the presence DDQ to afford compound 25 in an overall 75% yield. Suzuki−Miyaura cross-coupling reaction of compound 25 with (4-ethylphenyl)boronic acid in the presence of Pd(CH3CN)2Cl2, SPhos, and K3PO4 then furnished the
  • the prefused building block in a 49% yield. Then naphthalene and phenanthrene residues were introduced into compound 33 through Suzuki coupling reaction, the corresponding precursors 34 and 36 were obtained respectively in high yields. The final cyclodehydrogenation using DDQ and TfOH proceeded
  • benzo[b]naphtho[2,3-f]oxepine 66 with tetrabromothiophene-S,S-dioxide in toluene followed by oxidative aromatization in the presence of DDQ afforded tetrabrominated aromatics 67 in an 81% yield. Subsequently, fourfold Suzuki–Miyaura cross-coupling of polybrominated compound 67 was performed, affording
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Published 30 May 2023

Strategies in the synthesis of dibenzo[b,f]heteropines

  • David I. H. Maier,
  • Barend C. B. Bezuidenhoudt and
  • Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

Graphical Abstract
  • . through a multicomponent reaction system [57]. The authors provided a series of substituted derivatives through Pd/Rh-catalysed domino coupling. The reaction proceeded via a Suzuki coupling, followed by an in situ Buchwald–Hartwig amination. The authors reported moderate to good yields in a series with
  • electron-donating and electron-withdrawing groups, as well as N-aryl and N-alkylamines (Scheme 15). Lam et al. [58] expanded on the multicomponent method to form substituted dihydropyridobenzazepines 80–82 wherein vinylpyridines 77 are coupled with boronate ester anilines 78 in a Suzuki reaction
  • towards dibenzo[b,f]azepines and other dibenzo[b,f]heteropines, and the functionalisation thereof. Modern metal-catalyzed methods to introduce the C–C bridge include the Heck reaction, the Sonogashira reaction, Suzuki coupling and ring-closing metathesis, whereas Buchwald–Hartwig type reactions and Ullman
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Published 22 May 2023
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