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Search for "coupling reaction" in Full Text gives 510 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions

  • Akihiro Yuasa,
  • Kazunori Nagao and
  • Hirohisa Ohmiya

Beilstein J. Org. Chem. 2020, 16, 185–189, doi:10.3762/bjoc.16.21

Graphical Abstract
  • homoallylic alcohol derivatives [12][13][14]. Results and Discussion Specifically, the three-component allylic cross-coupling reaction of benzaldehyde (1a, 0.4 mmol), tert-butyl cinnamyl carbonate (2a, 0.2 mmol) and (dimethylphenylsilyl)boronic acid pinacol ester [PhMe2SiB(pin)] (0.4 mmol) occurred in the
  • silyl ether, which are derived from the Pd-catalyzed allylic silylation of 2a and the Cu-catalyzed silylation of 1a and the subsequent [1,2]-Brook rearrangement, respectively. In this coupling reaction, (SIPr)CuCl was a slightly better copper complex than (IPr)CuCl (62%), (SIMes)CuCl (60%) and (IMes
  • )CuCl (53%) in terms of the chemical yield. Notably, the allylic cross-coupling reaction did not occur at all without Pd(OCOCF3)2–DPPF or (SIPr)CuCl, and thus the palladium and copper catalysts cooperatively acted in the allylic cross-coupling. Scheme 3 shows the substrate range of aromatic aldehydes 1
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Published 07 Feb 2020

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

  • Andreas H. Heindl and
  • Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

Graphical Abstract
  • ]. Additionally, starting from easily accessible 3,5-dibromoazobenzenes H, only two consecutive coupling reactions, followed by oxidation, would be required to obtain the target starazo 3. However, selectivity might be problematic in the first coupling reaction, which would lead to lower yields of the desired
  • coupling reaction was assayed [10][11]. In order to investigate the applicability of the Pd-catalyzed route to C2-symmetric compounds, 1,3-bis(4-methoxyphenylazo)-5-phenylazobenzene (14) was targeted. First, via coupling of 3,5-dibromoazobenzene (11) [22][23] using 2.2 equiv of 4-methoxyphenyl-N-Boc
  • precursors 17a in 23% and 17b in 52% yield, respectively (Scheme 5). Again, like for the first coupling reaction, it was not possible to isolate the products as uniform isomers using chromatographic methods. Hence, the tris(arylazo)benzene precursors 17a/17b were used without further purification. Initially
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Published 03 Jan 2020

Functionalization of the imidazo[1,2-a]pyridine ring in α-phosphonoacrylates and α-phosphonopropionates via microwave-assisted Mizoroki–Heck reaction

  • Damian Kusy,
  • Agata Wojciechowska,
  • Joanna Małolepsza and
  • Katarzyna M. Błażewska

Beilstein J. Org. Chem. 2020, 16, 15–21, doi:10.3762/bjoc.16.3

Graphical Abstract
  • heterogeneous and homogeneous catalysts, as well as continuous-flow conditions [13][14][15]. Therefore, we tested microwave heating, a technique which is known for significant acceleration of the C–C coupling reaction [16]. We carried out the optimization studies using model substrates – compound 1a and benzyl
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Published 03 Jan 2020

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

  • László Orha,
  • József M. Tukacs,
  • László Kollár and
  • László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

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  • chemistry; ionic liquids; Introduction In the past few decades, the transition-metal-catalyzed coupling reaction has represented one of the most powerful and atom economical strategies for the efficient assembly of new carbon–carbon bonds. It has therefore become the most attractive approach to the
  • wide applicability from syntheses of common building blocks to agrochemicals, just to name a few advantages [4][5][6]. From the series of palladium-assisted C–C bond formation, the Sonogashira coupling reaction has been identified as a viable synthetic method for the preparation of various alkenyl- and
  • excluding the copper impurities assisted Ullmann-coupling reactions. When 2-chloro-5-iodopyridine (1l) was reacted with 1 equiv of 2, 2-chloro-5-(2-phenylethynyl)pyridine (3l) was isolated as product with a yield of 72%. By the use of 2.5 equiv of 2, the chloro group also undergoes a coupling reaction to
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Published 03 Dec 2019

Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

  • Sara Tejera,
  • Giada Caniglia,
  • Rosa L. Dorta,
  • Andrea Favero,
  • Javier González-Platas and
  • Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

Graphical Abstract
  • from the corresponding alkynes and diazides 5 and 6, respectively. In this context, it was required to isolate 5 and 6 before the coupling reaction could be performed. Compounds 9 and 10 (Scheme 3) were obtained in good yields by treatment of 7f and 8f, respectively, with sodium methoxide in CH2Cl2
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Published 28 Nov 2019

Carbazole-functionalized hyper-cross-linked polymers for CO2 uptake based on Friedel–Crafts polymerization on 9-phenylcarbazole

  • Dandan Fang,
  • Xiaodong Li,
  • Meishuai Zou,
  • Xiaoyan Guo and
  • Aijuan Zhang

Beilstein J. Org. Chem. 2019, 15, 2856–2863, doi:10.3762/bjoc.15.279

Graphical Abstract
  • HCPs include solvent knitting methods [10], Scholl coupling reaction [11], the knitting method with formaldehyde dimethyl acetal (FDA) [12], functional group reactions [2][13] and so on. Among these methods, the knitting method with FDA as external cross-linker is the most time-efficient approach [14
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Published 26 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 Suzuki–Miyaura cross-coupling reaction with MIDA
  • group was most effectively achieved with a Suzuki–Miyaura 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
  • modifications include: (1) the introduction of the C7-cyclopropyl group was most effectively achieved with a Suzuki–Miyaura 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
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Published 19 Nov 2019

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

  • Constantin Stuckhardt,
  • Diederik Roke,
  • Wojciech Danowski,
  • Edwin Otten,
  • Sander J. Wezenberg and
  • Ben L. Feringa

Beilstein J. Org. Chem. 2019, 15, 2767–2773, doi:10.3762/bjoc.15.268

Graphical Abstract
  • formed revealing that a chiral self-sorting process takes place. In addition, two of the cage isomers can bind a tosylate anion in solution by formation of a host–guest complex. Results and Discussion Ligands Z-1 and E-1 (Scheme 1) were synthesized by a Suzuki cross-coupling reaction of 3
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Published 15 Nov 2019

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

  • Munmun Ghosh,
  • Valmik S. Shinde and
  • Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

Graphical Abstract
  • oxidation. The radical–radical coupling reaction between 101 and 95 is proposed to afford the corresponding intermediate 102. Then release of the Lewis acid catalyst gives the final product 97. The stereocontrol step is related to the in situ generation of radicals with π-systems of chiral enamines and
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Published 13 Nov 2019

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

  • Vânia F. Pais,
  • Tristan Neumann,
  • Ignacio Vayá,
  • M. Consuelo Jiménez,
  • Abel Ros and
  • Uwe Pischel

Beilstein J. Org. Chem. 2019, 15, 2612–2622, doi:10.3762/bjoc.15.254

Graphical Abstract
  • -coupling reactions was planned. Starting from 1-bromo-4-methoxynaphthalene (1), the Pd-catalyzed Suzuki coupling reaction with commercial boronic acids afforded the naphthyl and pyrenyl derived methyl ethers 2 and 3 in 78% and 87% yield, respectively (Scheme 1). For the synthesis of the anthryl derivative
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Published 04 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
  • catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction. Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines
  • –11b (Scheme 2) [22][28]. Hereby, the boroxines 9b–11b were accessible by thermal dehydration of the corresponding boronic acids 9a–11a. With this procedure product 13 was obtained in only 6% yield, which is presumably due to a competing coupling reaction of the boroxine moiety of 9b with the chlorine
  • atom of 9b or sterical reasons (the chlorine in 2’-position might lead to repulsion during the cross-coupling reaction). The reaction of the triflate with cyano-substituted phenylboroxines 10b and 11b led to silicon rhodamine dyes 14 and 15 in poor yields of 23 and 19%, respectively. The reaction
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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 Suzuki–Miyaura cross-coupling reaction. Notably, the yield was low (26%) [55], and the X-ray
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Published 17 Oct 2019

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

  • Sachin S. Burade,
  • Sushil V. Pawar,
  • Tanmoy Saha,
  • Navanath Kumbhar,
  • Amol S. Kotmale,
  • Manzoor Ahmad,
  • Pinaki Talukdar and
  • Dilip D. Dhavale

Beilstein J. Org. Chem. 2019, 15, 2419–2427, doi:10.3762/bjoc.15.234

Graphical Abstract
  • converted to amino acid di- and tetrapeptides 8 and 9, respectively, using hydrolysis followed by a hydrogenation reaction protocol (Scheme 2). In order to get cyclic peptides I and II (Figure 1), an individual intramolecular coupling reaction of linear dipeptide 8 and tetrapeptide 9 was attempted. Thus
  • functionalities are apart from each other. However, an individual intramolecular coupling reaction of 8 and 9 using CMPI as a coupling reagent, in the presence of Et3N in dichloromethane, afforded pseudodipeptide 1 and pseudotetrapeptide 2a, respectively, with oxazolone ring formation at the C-terminal of the
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Published 14 Oct 2019

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

Graphical Abstract
  • ]. Reaction of allyl iodide (17) with metalated 9d after addition of catalytic amounts of CuCN∙2LiCl led to the formation of the 5-allyl compound 18 in 37% yield. Metalation of 9d using TMPMgCl∙LiCl and subsequent transmetalation with ZnCl2 followed by Negishi cross-coupling reaction in the presence of Pd(dba
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Published 26 Sep 2019

Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene

  • Luna Kono,
  • Yuma Nakagawa,
  • Ayako Fujimoto,
  • Ryo Nishimura,
  • Yohei Hattori,
  • Toshiki Mutai,
  • Nobuhiro Yasuda,
  • Kenichi Koizumi,
  • Satoshi Yokojima,
  • Shinichiro Nakamura and
  • Kingo Uchida

Beilstein J. Org. Chem. 2019, 15, 2204–2212, doi:10.3762/bjoc.15.217

Graphical Abstract
  • , we prepared a diarylethene incorporating the imidazo[1,2-a]pyridine moiety with ESIPT ability and reported the fluorescence switching of the system. Results and Discussion The diarylethene 1o having an ESIPT moiety was prepared by a coupling reaction of asymmetric diarylethene 3 [24] and 6-bromo-2-(2
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Published 20 Sep 2019

Vicinal difunctionalization of alkenes by four-component radical cascade reaction of xanthogenates, alkenes, CO, and sulfonyl oxime ethers

  • Shuhei Sumino,
  • Takahide Fukuyama,
  • Mika Sasano,
  • Ilhyong Ryu,
  • Antoine Jacquet,
  • Frédéric Robert and
  • Yannick Landais

Beilstein J. Org. Chem. 2019, 15, 1822–1828, doi:10.3762/bjoc.15.176

Graphical Abstract
  • competent substrates in the present four-component coupling reaction, affording 5f, albeit in modest yield. The reaction of 1a with 6-heptenenitrile (2e) and 5-hexen-2-one (2f) gave the corresponding four-component coupling products 5g and 5h, in 34 and 41% yield, respectively. The reaction with cyano
  • -substituted sulfonyl oxime ester 3b also worked well to provide cyano-functionalized α-keto oximes. 5i, 5j, and 5k were thus accessible through the four-component coupling reaction between xanthogenates, alkenes, CO, and 3b in acceptable isolated yields (39–50%). Finally, the reaction between acetophenone
  • mechanism. Concept: Alkene difuctionalization by four-component radical reaction using xanthates, alkenes, CO and sulfonyl oxime ethers. Four-component coupling reaction of ethyl 2-((ethoxycarbonothioyl)thio)acetate (1a), 1-octene (2a), CO, and sulfonyl oxime ether 3a under radical conditionsa. Supporting
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Published 31 Jul 2019

Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

  • Roland Löw,
  • Talina Rusch,
  • Tobias Moje,
  • Fynn Röhricht,
  • Olaf M. Magnussen and
  • Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

Graphical Abstract
  • decomposition, which is a necessary precondition for ultra-high vacuum STM investigations. The 3-bromo-2-cyano-substituted norbornadiene 4 was synthesized as described in the literature (Scheme 1) [10][11][12]. 4 was converted to 5 with trimethylsilylacetylene (72%) in a Sonogashira cross-coupling reaction. The
  • obtained in a convergent synthesis (Scheme 2). Boronic ester 9 was synthesized as described in the literature [15]. In a Suzuki cross-coupling reaction norbornadiene 4 was coupled with 9 to the extended norbornadiene 10 (38%), which was attached to the TATA platform 6 to yield the extended norbornadiene
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Published 30 Jul 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
  • coupling reaction for the synthesis of 2-triazolylimidazo[1,2-a]pyridine 74 (Scheme 26) [31]. The reaction involved the use of copper oxide as a catalyst and sodium ascorbate as a reducing agent using triazolyl aldehyde 73, amidine 3 and terminal alkynes 2 as reaction substrates at 70 °C (Scheme 26). Here
  • of the common reactants with 2-aminopyridines/2-aminoquinolines/1-aminoisoquinolines 3, 75, 76 to give the desired products, respectively (Scheme 27). Both EWGs and EDGs on the reactants resulted in good to excellent yields of the product. This process followed two types of coupling reaction
  • protocol also provided a concise route for the synthesis of the antiulcer drug zolimidine in 95% yield. A three-component coupling reaction (3-CCR) for the synthesis of N-fused pyridines was reported by Balijapalli and Iyer [40]. The reaction was catalyzed by CuO/CuAl2O4 and ᴅ-glucose. The reaction had
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Published 19 Jul 2019

Synthesis of 9-O-arylated berberines via copper-catalyzed CAr–O coupling reactions

  • Qiaoqiao Teng,
  • Xinhui Zhu,
  • Qianqian Guo,
  • Weihua Jiang,
  • Jiang Liu and
  • Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

Graphical Abstract
  • leading to the failure of direct BBRB cross coupling. 9-O-Aryl berberine scope via cross-coupling reaction. 9-O-Ph-linked berberine dimer through double cross-coupling reaction. Optimization of the reaction conditions.a Supporting Information Supporting Information File 138: Experimental details and
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Published 15 Jul 2019

Diazocine-functionalized TATA platforms

  • Roland Löw,
  • Talina Rusch,
  • Fynn Röhricht,
  • Olaf Magnussen and
  • Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1485–1490, doi:10.3762/bjoc.15.150

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  • a function of electronic coupling (conjugation) of the azo unit to gold. The para-diazocine-TATA 1 was synthesized in a 5-step synthesis route (Scheme 1). Bromotoluene 3 was synthesized as described [26]. In a Sonogashira cross-coupling reaction acetylene-substituted toluene 5 was prepared from
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Published 05 Jul 2019

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

  • Pierre-Olivier Schwartz,
  • Sebastian Förtsch,
  • Astrid Vogt,
  • Elena Mena-Osteritz and
  • Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

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  • starting material, but also ring fusion to selenophene was achieved by Cu-catalyzed C–Se cross-coupling reaction [28]. The detailed geometric structure and the packing behaviour in the solid state of triacenes 2–4 have been elucidated by single crystal X-ray structure analysis and X-ray diffraction on
  • reinvestigated the synthesis of DTT 1 by using a Cu-catalyzed C–S cross-coupling reaction with potassium sulfide (K2S) as sulfur source [29]. The best results for this C–S ring-closure reaction were achieved by reacting 3,3’-diiodo-2,2’-bithiophene (5) [30] with the system K2S and copper iodide (CuI) as catalyst
  • deprotection with TBAF in 66% yield, with selenourea and copper oxide nanoparticles surprisingly did not lead to any targeted DSS 4 in the attempted C–Se cross-coupling reaction. The structures of the prepared novel selenolotriacenes 2–4 and known DTT 1 were characterized by means of NMR spectroscopy
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Published 24 Jun 2019

Selective detection of DABCO using a supramolecular interconversion as fluorescence reporter

  • Indrajit Paul,
  • Debabrata Samanta,
  • Sudhakar Gaikwad and
  • Michael Schmittel

Beilstein J. Org. Chem. 2019, 15, 1371–1378, doi:10.3762/bjoc.15.137

Graphical Abstract
  • in Scheme 1. Therefore, ligands 1 and 2 were synthesized by a palladium-catalyzed Sonogashira coupling reaction (Supporting Information File 1). All compounds were fully characterized by 1H NMR, 1H,1H-COSY, UV–vis, ESIMS and elemental analysis (Supporting Information File 1). Subsequently, we
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Published 21 Jun 2019

N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe3+ sensing

  • Jia Gao,
  • Ming-Xue Wu,
  • Dihua Dai,
  • Zhi Cai,
  • Yue Wang,
  • Wenhui Fang,
  • Yan Wang and
  • Ying-Wei Yang

Beilstein J. Org. Chem. 2019, 15, 1262–1267, doi:10.3762/bjoc.15.123

Graphical Abstract
  • ) through covalent bonds formed by EDC-NHS coupling reaction. The comparison of CCDs with single CN-dots without CP[5], revealed that the CCDs exhibit a higher selectivity for Fe3+ detection (Scheme 1). Fe3+ ions play an important role in the living organism and is related to many diseases, thus it is vital
  • surface of CN-dots via EDC-NHS coupling reaction. Compared with unmodified CN-dots, CCDs demonstrated novel properties after the introduction of CP[5], and showed a higher selective sensing ability for Fe3+ ions. Hopefully, this strategy will inspire the design of new fluorescent chemical sensors toward
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Published 07 Jun 2019

Insertion of [1.1.1]propellane into aromatic disulfides

  • Robin M. Bär,
  • Gregor Heinrich,
  • Martin Nieger,
  • Olaf Fuhr and
  • Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

Graphical Abstract
  • opening of 1 with Grignard reagents enables the synthesis of aryl and some alkyl-substituted BCPs and a subsequent cross-coupling reaction [5][18]. To provide bicyclo[1.1.1]pentylamine as a building block in large-scale syntheses, Bunker et al. developed a synthesis of hydrazine BCP via a manganese
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Published 28 May 2019

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

  • Edorta Martínez de Marigorta,
  • Jesús M. de Los Santos,
  • Ana M. Ochoa de Retana,
  • Javier Vicario and
  • Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

Graphical Abstract
  • palladium-catalysed reactions (Scheme 38). The first one is a Sonogashira coupling reaction between the terminal alkyne of propiolamide 128 and aryl iodide 129, which is preferred to the Suzuki–Miyaura reaction between aryl iodide 129 and boronic acid 130 present in the reaction mixture. Then, an internal
  • series of 3-methyleneisoindolin-1-ones 13 were obtained (Scheme 2) [77]. Several aromatic and heteroaromatic substituents can be introduced in the exocyclic methylene position with high regioselectivity. It is noteworthy that arylalkynylcarboxilic acids 11 (R2 = Ar) can be obtained easily by the coupling
  • reaction of propiolic acid and aryl halides [78]. Furthermore, the authors have been able to carry out the reaction in a sequential manner starting from propiolic acid and aryl iodides in the presence of caesium carbonate and a palladium catalyst. Next, addition of 2-iodobenzoic acid and ammonium acetate
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Published 08 May 2019
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