Search results

Search for "Suzuki–Miyaura" in Full Text gives 184 result(s) in Beilstein Journal of Organic Chemistry.

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization

  • Sharna-kay Daley and
  • Nadale Downer-Riley

Beilstein J. Org. Chem. 2020, 16, 2026–2031, doi:10.3762/bjoc.16.169

Graphical Abstract
  • Ullman coupling, SuzukiMiyaura coupling and Stille coupling have dominated the field for the synthesis of biaryls [1][4]. Throughout the years, the exploration of oxidative dimerization reactions of electron-rich aromatic compounds, such as thiophenes, anilines and alkoxyarenes, in an attempt to
PDF
Album
Supp Info
Full Research Paper
Published 18 Aug 2020

Syntheses of spliceostatins and thailanstatins: a review

  • William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

Graphical Abstract
  • . The removal of the silyl protecting group and hydrolysis of the methyl ester afforded the carboxylic acid 108. A subsequently attempted SuzukiMiyaura coupling of 108 with vinyl boronates was described as “capricious”, and thus the acid was esterified with the tert-butyl donor reagent 109 to afford
  • utilized the sequential application of a cross-metathesis and a SuzukiMiyaura coupling in the syntheses of thailanstatin A and B (7 and 5) and spliceostatin D (9, Scheme 24) [24][25]. To this end, the methylhydrazinolysis of the phthalimide 39 and the amide formation with 12c yielded 121. The cross
  • -metathesis of 121 with a five-fold excess of isopropenylboronic acid pinacol ester afforded the lynchpin vinylborane 130. A Pd-catalyzed SuzukiMiyaura coupling of 130 with the vinyl iodide 110, 111, or 112 gave the tert-butyl ester 131, 132, or 133 in a moderate yield (42–63%). The hydrolysis of the tert
PDF
Album
Review
Published 13 Aug 2020

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

  • Paola Vitale,
  • Luciana Cicco,
  • Ilaria Cellamare,
  • Filippo M. Perna,
  • Antonio Salomone and
  • Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

Graphical Abstract
  • ], (c) carbon–sulfur bond-forming reactions [9], (d) directed ortho-metalation and nucleophilic acyl substitution strategies [10], (e) Pd-catalyzed aminocarbonylation of aryl iodides, SuzukiMiyaura and Sonogashira cross-coupling reactions [11][12][13], (f) Cu-catalyzed C–N coupling reactions [14], and
PDF
Album
Supp Info
Full Research Paper
Published 05 Aug 2020

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

  • Haruyasu Asahara,
  • Minami Hiraishi and
  • Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

Graphical Abstract
  • group hinder the electrophilic modification at the 3-position. Generally, the aryl group is introduced by a SuzukiMiyaura cross-coupling reaction [4][5], for which 3-bromo-4-nitrophenol must be prepared by the nitration of 3-bromophenol [6][7]. An alternative approach is the nitration of 3-arylphenol
PDF
Album
Supp Info
Full Research Paper
Published 22 Jul 2020

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

  • Valeria Nori,
  • Antonio Arcadi,
  • Armando Carlone,
  • Fabio Marinelli and
  • Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

Graphical Abstract
  • (Te), Italy 10.3762/bjoc.16.95 Abstract Cascade cyclocarbopalladation of the readily available aryl/alkyl-substituted propargylic amides containing an aryl iodide moiety, followed by SuzukiMiyaura coupling with arylboronic acids, allowed an efficient regio- and stereoselective synthesis of
  • 4 and 6 was unambiguously confirmed by NMR spectroscopy [43]. Conclusion In conclusion, we have demonstrated that cascade cyclocarbopalladations of the readily available aryl/alkyl-substituted N-propargyl-2-iodobenzamides 2 followed by SuzukiMiyaura coupling reactions with arylboronic acids, in the
PDF
Album
Supp Info
Full Research Paper
Published 20 May 2020

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

  • Nuray Altinolcek,
  • Ahmet Battal,
  • Mustafa Tavasli,
  • William J. Peveler,
  • Holly A. Yu and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

Graphical Abstract
  • potassium acetate (KOAc) and dichlorobis(triphenylphosphine)palladium(II) in 1,4-dioxane [36][37]. Upon chromatography (9-hexylcarbazole-3-yl)boronic acid pinacol ester (5) was obtained as a liquid in good yield. (9-Hexylcarbazole-3-yl)boronic acid pinacol ester (5) was subjected to SuzukiMiyaura reaction
PDF
Album
Supp Info
Full Research Paper
Published 19 May 2020

Suzuki–Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents

  • James Sherwood

Beilstein J. Org. Chem. 2020, 16, 1001–1005, doi:10.3762/bjoc.16.89

Graphical Abstract
  • conventional solvents. In this work, the suitability of the SuzukiMiyaura reaction to demonstrate the usefulness of new solvents was evaluated, including Cyrene™, dimethyl isosorbide, ethyl lactate, 2-methyltetrahydrofuran (2-MeTHF), propylene carbonate, and γ-valerolactone (GVL). It was found that the cross
  • coupling is often unaffected by the choice of solvent, and therefore the SuzukiMiyaura reaction provides limited information regarding the usefulness of any particular solvent for organic synthesis. Keywords: cross coupling; green solvents; palladium; solvent selection; Suzuki reaction; Findings The
  • objective of this work was to reveal if there is a relationship between the productivity of SuzukiMiyaura cross couplings and the properties of the solvent, and whether this could be used to justify solvent selection. The choice of solvent is one variable that dictates reaction rate, selectivity
PDF
Album
Supp Info
Letter
Published 13 May 2020

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

  • Yongsu Li,
  • Bendu Pan,
  • Xuefeng He,
  • Wang Xia,
  • Yaqi Zhang,
  • Hao Liang,
  • Chitreddy V. Subba Reddy,
  • Rihui Cao and
  • Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

Graphical Abstract
  • Abstract Pd-catalyzed asymmetric SuzukiMiyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good
  • bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity. Keywords: asymmetric catalysis; biaryls; monophosphine ligand; palladium catalyst; SuzukiMiyaura couplings; Introduction Axially chiral molecules have received much attention
  • efficient synthesis of this scaffold [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22], like Hiyama [23][24], Negishi [25][26] or SuzukiMiyaura couplings [27][28][29][30][31][32][33][34][35][36]. In these synthetic strategies, the reaction system of palladium with chiral phosphine ligands was
PDF
Album
Supp Info
Full Research Paper
Published 11 May 2020

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

  • Valerian Dragutan,
  • Ileana Dragutan,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

Graphical Abstract
  • to build the desired 1,3-dienic units. The advantageous association of this approach with name reactions like Grignard, Wittig, Diels–Alder, SuzukiMiyaura, Heck cross-coupling, etc. is illustrated. Examples unveil the generality of such tandem reactions in providing not only the intricate structures
  • ][39][40][41][42][43]. In ingeniously elaborated procedures, olefin metathesis has been frequently employed as such or associated with name reactions like Grignard, Wittig, Diels–Alder, SuzukiMiyaura, Heck, etc., resulting in the assembly of diverse intricate building blocks of the targeted structures
  • of the dienic compound through a SuzukiMiyaura coupling and Julia–Kocienski olefination, followed by a Yamaguchi lactonization, and an asymmetric epoxidation in the presence of (+)-diethyl tartrate, conveniently produced (−)-amphidinolide K (4, Scheme 7). In a remarkable work, Trost et al. [72
PDF
Album
Review
Published 16 Apr 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

Graphical Abstract
PDF
Album
Review
Published 15 Apr 2020

Direct borylation of terrylene and quaterrylene

  • Haruka Kano,
  • Keiji Uehara,
  • Kyohei Matsuo,
  • Hironobu Hayashi,
  • Hiroko Yamada and
  • Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

Graphical Abstract
  • hinderance of Bpin moieties. Finally, to demonstrate the utility of the borylated oligorylenes, the SuzukiMiyaura cross-coupling reaction of TB4 under the standard conditions was performed (Scheme 3). Coupling of TB4 and 2-bromomesitylene with Pd(PPh3)4, Cs2CO3 and CsF in a mixture of toluene/DMF furnished
  • -dioxaborolan-2-yl. Synthesis of 2,5,12,15-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quaterrylene (QB4): (a) (Bpin)2 (12 equiv), [Ir(OMe)cod]2 (20 mol %), di-tert-butylbipyridyl (40 mol %), 1,4-dioxane, at 105 °C, 38 h, yield 0.4%. SuzukiMiyaura cross-coupling reaction of TB4 with 2-bromomesitylene
PDF
Album
Supp Info
Letter
Published 06 Apr 2020

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

  • Pezhman Shiri and
  • Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Graphical Abstract
  • /mechanical stability, and good adsorption capacity. They also contain an ordered porous network that is appropriate for the free diffusion of reactants and reaction products [24]. In this regard, various functionalized SiO2 nanoparticles were employed in diverse organic reactions, including SuzukiMiyaura
  • delivery [93], and cancer detection [94]. In this regard, various functionalized MNPs were employed in diverse organic reactions, including SuzukiMiyaura reactions, Sonogashira reactions, Ullmann coupling, hydrogenation reactions, oxidation reactions, hydroformylation reactions, and “click” reactions [89
PDF
Album
Review
Published 01 Apr 2020

Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives

  • Seiya Terai,
  • Yuki Sato,
  • Takuya Kochi and
  • Fumitoshi Kakiuchi

Beilstein J. Org. Chem. 2020, 16, 544–550, doi:10.3762/bjoc.16.51

Graphical Abstract
  • reaction, followed by dehydrogenative photocyclization, and FeCl3-mediated oxidative cyclization (Scheme 2a) [43]. Tao, Chao, and co-workers succeeded in the preparation of similar tetrasubstituted tetrabenzocoronenes by a Corey–Fuchs reaction, followed by a SuzukiMiyaura cross-coupling, and a two-step
PDF
Album
Supp Info
Full Research Paper
Published 31 Mar 2020

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

  • Md. Shafiqur Rahman and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

Graphical Abstract
  • via 1,4-cobalt migration. The resulting 7-hydroxybenzo[b]phosphole derivative was used for further π-extension through SuzukiMiyaura couplings and a Scholl reaction, the latter closing the triphenylene ring. The absorption and emission spectra of the thus-synthesized compounds illustrated their
  • π-extension through a SuzukiMiyaura coupling, Sonogashira coupling, and electrophilic alkyne carbocyclization [18]. Given the successful synthesis of the angularly fused phosphahelicenes, we became interested in the further exploitation of 7-hydroxybenzo[b]phosphole as an intermediate for the
  • converted to the triflate, and subjected to SuzukiMiyaura couplings with 2-bromophenylboronic acid (5a) or 3-bromonaphth-2-ylboronic acid (5b) to afford the phosphole-fused biaryls 6a and 6b, respectively, in decent yields. Subsequent SuzukiMiyaura couplings of 6a or 6b with 3,4-dialkoxyarylboronic acids
PDF
Album
Supp Info
Letter
Published 27 Mar 2020

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

  • Vuyisa Mzozoyana,
  • Fanie R. van Heerden and
  • Craig Grimmer

Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22

Graphical Abstract
  • , numerous methods for the synthesis of these compounds have been developed, examples are the Pechmann condensation [10][11], Stille coupling reaction [12], Knoevenagel condensation [13], Heck coupling reaction [14], Kostanecki reaction, Baylis–Hillman reaction [15], Michael reaction [16], SuzukiMiyaura
PDF
Album
Supp Info
Full Research Paper
Published 10 Feb 2020

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

  • Hoang Huy Do,
  • Saif Ullah,
  • Alexander Villinger,
  • Joanna Lecka,
  • Jean Sévigny,
  • Peter Ehlers,
  • Jamshed Iqbal and
  • Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

Graphical Abstract
  • , Québec, QC, G1V 4G2, Canada Leibniz-Institut für Katalyse an der Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany 10.3762/bjoc.15.276 Abstract A two-step palladium-catalyzed procedure based on SuzukiMiyaura cross coupling, followed by a double Buchwald–Hartwig reaction, allows
  • results were rationalized based on docking studies. Keywords: Buchwald–Hartwig reaction; cyclization; N-heterocycles; palladium; SuzukiMiyaura reaction; Introduction Furoindoles and their derivatives have received a lot of attention based on their versatile pharmaceutical activities. Furoindols were
  • diindolofurans by regioselective SuzukiMiyaura couplings of tetrabromofuran and subsequent cyclization by tetrafold Buchwald–Hartwig reaction [31]. We also studied the synthesis of benzo[4,5]furo[3,2-b]indoles by a similar concept. However, while performing our studies, Truong et al. reported the synthesis of
PDF
Album
Supp Info
Full Research Paper
Published 22 Nov 2019

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

  • Nicky J. Willis,
  • Elliott D. Bayle,
  • George Papageorgiou,
  • David Steadman,
  • Benjamin N. Atkinson,
  • William Mahy and
  • Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

Graphical Abstract
  • biology of Notum and build target validation to underpin new drug discovery programs. Results: An improved, scalable synthesis of 1 is reported. Key modifications include: (1) the introduction of the C7-cyclopropyl group was most effectively achieved with a SuzukiMiyaura cross-coupling reaction with MIDA
  • group was most effectively achieved with a SuzukiMiyaura cross-coupling reaction with MIDA-boronate 11 (5 → 6); and (2) C6 chlorination was performed with 1-chloro-1,2-benziodoxol-3-one (12) (6 → 7) as a mild selective electrophilic chlorination agent. 4-Chlorothieno[3,2-d]pyrimidine (3) was either
  • efficient step in our sequence and justified further optimisation (vide infra). SuzukiMiyaura cross coupling of bromide 5 with cyclopropylboronic acid (2.5 equiv) produced 6 in good yield (62–89%) but the product required extensive chromatographic purification. We reasoned that switching from the boronic
PDF
Album
Supp Info
Full Research Paper
Published 19 Nov 2019

Progress in metathesis chemistry

  • Karol Grela and
  • Anna Kajetanowicz

Beilstein J. Org. Chem. 2019, 15, 2765–2766, doi:10.3762/bjoc.15.267

Graphical Abstract
  • catalysts work and decompose, how macrocycles are formed in ring-closing metathesis, etc. Representative examples of these directions have been the subject of the current, third thematic issue on Olefin Metathesis, including highly educative reviews on tandem olefin metathesis–SuzukiMiyaura cross coupling
PDF
Editorial
Published 15 Nov 2019

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

  • Sarah L. Skraba-Joiner,
  • Carter J. Holt and
  • Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

Graphical Abstract
  • , samples of m,p’- (13), o,p’- (15), o,m’- (16), and o,o’-quaterphenyl (17) were synthesized as shown in Scheme 3. SuzukiMiyaura coupling was used to synthesize 13, 15, and 16 from the corresponding aryl bromides and boronic acids [35]. o,o’-Quaterphenyl (17) was synthesized by homo-coupling of 2
  • through time-of-flight matrix assisted laser desorption ionization (MALDI–TOF–MS) mass spectrometry, using sulfur as a matrix. SuzukiMiyaura coupling to form m,p’-quaterphenyl (13) [35]: 4-Biphenylboronic acid (0.18 g, 0.91 mmol) and 1 M K2CO3 (1.5 mL) were added to a 10 mL Pyrex microwave tube. 3
  • (400 MHz, CDCl3) δ 7.87–7.85 (m, 1H), 7.76–7.69 (m, 4H), 7.69–7.64 (m, 4H), 7.64–7.58 (m, 2H), 7.57–7.52 (m, 1H), 7.50–7.45 (m, 4H), 7.41–7.35 (m, 2H). SuzukiMiyaura coupling to form o,p’-quaterphenyl (15) [35]: K2CO3 (0.91 g, 6.6 mmol) and water (7.7 mL) were combined in a 25 mL round bottom flask
PDF
Album
Supp Info
Full Research Paper
Published 06 Nov 2019

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

  • Thines Kanagasundaram,
  • Antje Timmermann,
  • Carsten S. Kramer and
  • Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

Graphical Abstract
  • application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which SuzukiMiyaura cross couplings
  • functionalized with free acid moieties are directly accessible in contrast to previously described methods. Keywords: cross coupling; fluorescent dyes; near-infrared (NIR) dyes; silicon rhodamines; SuzukiMiyaura coupling; Introduction Silicon rhodamines are versatile fluorescent dyes that found extensive use
  • , we wanted to investigate if these dyes are also accessible by SuzukiMiyaura coupling. Results and Discussion Optimization of reaction conditions At first we investigated the effects of different catalysts and boron compounds on the synthesis of silicon rhodamine 22 via SuzukiMiyaura cross coupling
PDF
Album
Supp Info
Full Research Paper
Published 29 Oct 2019

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

  • Zhen Cao,
  • Aline Lacoudre,
  • Cybille Rossy and
  • Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

Graphical Abstract
  • reactions of alkynes. Results and Discussion Synthesis of silver(I) complexes Ligand 1 was synthesized in one step, from commercially available 9,10-dibromoanthracene and 2-(methylthio)phenylboronic acid, using a SuzukiMiyaura cross-coupling reaction. Notably, the yield was low (26%) [55], and the X-ray
PDF
Album
Supp Info
Full Research Paper
Published 17 Oct 2019

Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms

  • A. Lennart Schleper,
  • Mariano L. Bossi,
  • Vladimir N. Belov and
  • Stefan W. Hell

Beilstein J. Org. Chem. 2019, 15, 2344–2354, doi:10.3762/bjoc.15.227

Graphical Abstract
  • regioisomeric bromides were also formed, but they were separated by column chromatography on the next step. Bithiophene 11 was prepared in 74% yield by using a SuzukiMiyaura coupling (catalyzed by PEPPSI-IPr) between boronic ester 9 and bromide 10 [13][14]. Boronation of bithiophene 11 was achieved under
  • , AsOTh2, and SyOTh2 (Figure 1) were obtained using a standard procedure for a SuzukiMiyaura coupling of iodides 4, 5, 7, and 8 with boronic acid esters 9 and 12 (see Scheme 3). Throughout the text, abbreviations “As” and “Sy” denote asymmetric and symmetric substitution patterns, respectively; “O
  • esters 9 and 12 (bpy – 4,4’-di-tert-butyl-2,2’-dipyridine; COD – cycloocta-1,5-diene; NBS – N-bromosuccinimide, DCM – dichloromethane). Photoswitchable diarylethenes AsTh1, SyTh1, AsTh2, SyTh2, AsOTh1, SyOTh1, AsOTh2, and SyOTh2 synthesized via a SuzukiMiyaura coupling. Conditions: 60 °C, argon
PDF
Album
Supp Info
Full Research Paper
Published 01 Oct 2019

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

  • Christoph W. Grathwol,
  • Nathalie Wössner,
  • Sören Swyter,
  • Adam C. Smith,
  • Enrico Tapavicza,
  • Robert K. Hofstetter,
  • Anja Bodtke,
  • Manfred Jung and
  • Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

Graphical Abstract
  • ) as alkene component had detrimental effects on the yields in the synthesis of 2d, 2f and 2h. Intermediates 5a and 5b were accessible from 3a and 3b via SuzukiMiyaura or Stille coupling [34]. Biology The influence on deacetylase activity of three human sirtuin isoforms (Sirt1–3) was determined in a
PDF
Album
Supp Info
Full Research Paper
Published 16 Sep 2019

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Graphical Abstract
  • -catalyzed cross-coupling reactions have laid down the foundation of new C–C bond formations [50][51]. A number of Pd-catalyzed organic reactions viz., C–N coupling, amination and intramolecular amidation, cyclization, and SuzukiMiyaura coupling [52][53][54][55] have recently been reported in the literature
PDF
Album
Review
Published 19 Jul 2019

Synthesis of pyrrolo[1,2-a]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts

  • Anthony Choi,
  • Rebecca M. Morley and
  • Iain Coldham

Beilstein J. Org. Chem. 2019, 15, 1480–1484, doi:10.3762/bjoc.15.149

Graphical Abstract
  • could be converted to other derivatives by SuzukiMiyaura coupling, reduction or oxidation reactions. Keywords: azomethine ylide; cycloaddition; heterocycle; pyrrolidine; stereoselective; Introduction Cycloaddition reactions of azomethine ylides are an important class of pericyclic reactions that give
  • ). The adducts could be reduced, oxidised, or could undergo SuzukiMiyaura coupling to give different substituted dihydro- and tetrahydroquinoline derivatives. Single crystal X-ray structure for 7c. Single crystal X-ray structure for 9. Reaction of ketone 1 with electron-deficient alkenes 2. Reactions of
  • ester 4 and amide 5 with electron-deficient alkenes 6. Reactions of ester 4 and amide 5 with N-methylmaleimide. Reduction and oxidation of adducts 9 and 10. Formation of amides 15a and 15b and SuzukiMiyaura coupling to yield 16. Supporting Information Supporting Information File 322: Experimental
PDF
Album
Supp Info
Full Research Paper
Published 03 Jul 2019
Other Beilstein-Institut Open Science Activities