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Search for "cross-coupling reactions" in Full Text gives 298 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

  • Siva Sankar Murthy Bandaru,
  • Darinka Dzubiel,
  • Heiko Ihmels,
  • Mohebodin Karbasiyoun,
  • Mohamed M. A. Mahmoud and
  • Carola Schulzke

Beilstein J. Org. Chem. 2018, 14, 1871–1884, doi:10.3762/bjoc.14.161

Graphical Abstract
  • functionalization are necessary. In this context, Palladium-mediated cross-coupling reactions provide a powerful tool [21][22][23][24][25][26][27]; specifically, as these C–C coupling reactions have been demonstrated to be very useful for the introduction of various substituents to quinolizinium [28][29][30][31][32
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Published 23 Jul 2018

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

  • Alphonse Fiebor,
  • Richard Tia,
  • Banothile C. E. Makhubela and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

Graphical Abstract
  • investigation of their catalytic activity in the aqueous Suzuki–Miyaura coupling reaction. Herein, we report the synthesis of the SNS Pd(II) pincer complexes and their interesting catalytic activities in the Suzuki–Miyaura cross coupling reactions in neat water. Results and Discussion Our study commenced with
  • ), alkylphosphine (PCP) and aminophosphine (PCP) pincer complexes, and in each of these cases, catalysis was unaffected by metallic mercury during the cross-coupling reactions [41][42][43]. In addition, stable Pd(IV) complexes have been widely prepared and characterised, thus for the catalysis of the pincer
  • of the Suzuki–Miyaura cross coupling reaction of 4-bromoanisole (21a) and phenylboronic acid (22a). Results from the Suzuki–Miyaura cross-coupling reactions of various aryl bromides and boronic acids using pincer complex 17d as catalyst.a Supporting Information Supporting Information File 391
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Published 23 Jul 2018

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

  • Irina A. Mironova,
  • Pavel S. Postnikov,
  • Rosa Y. Yusubova,
  • Akira Yoshimura,
  • Thomas Wirth,
  • Viktor V. Zhdankin,
  • Victor N. Nemykin and
  • Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

Graphical Abstract
  • of phenols to 1,2-quinones [15], the cyclization and cross-coupling reactions [16], and the site-selective hydroxylative dearomatization of 2-substituted phenols to either 1,2-benzoquinols or their cyclodimers [17]. The first preparation and isolation of IBS (1) was attempted in 2006 using two
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Published 20 Jul 2018

Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

  • Eric Detmar,
  • Valentin Müller,
  • Daniel Zell,
  • Lutz Ackermann and
  • Martin Breugst

Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

Graphical Abstract
  • C–H functionalizations [18][19][20][21][22][23]. Similarly, computational studies revealed the importance of dispersion effects in palladium-catalyzed cross-coupling reactions [24][25][26][27]. For example, the contribution of London dispersion (up to 37 kcal mol−1) has a huge influence on the
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Published 25 Jun 2018

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

  • Gwendal Grelier,
  • Benjamin Darses and
  • Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

Graphical Abstract
  • , their reactivity is higher than that of the corresponding aryl halides, a property that has been widely exploited to develop efficient transition-metal-catalyzed cross coupling reactions [55]. The latter, however, allow for transferring only one of the two aromatic motifs of the iodonium reagents
  • first study documenting the coupling of both aromatic groups of a diaryl-λ3-iodane has been reported in 1995 by Bumagin and co-workers [25]. One equivalent of symmetrical diaryl-λ3-iodanes could be engaged in palladium-catalyzed cross-coupling reactions with 0.55 equivalent of sodium tetraphenylborate
  • , gives access to various iodoaminated intermediates that can be subsequently engaged in palladium-catalyzed Suzuki–Miyaura, Sonogashira, or Mizoroki–Heck cross-coupling reactions. Various aryl, alkenyl, or alkynyl substituents can thus be introduced in good to very good yields. When compared to the
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Published 21 Jun 2018

Atom-economical group-transfer reactions with hypervalent iodine compounds

  • Andreas Boelke,
  • Peter Finkbeiner and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

Graphical Abstract
  • lead to an overall AE of up to 70% but also produces synthetically versatile intermediates for subsequent transformations, in particular metal-catalyzed cross-coupling reactions. If benziodoxolones or benziodoxoles are used as group-transfer reagents, nearly 100% AE is possible since the counterion
  • , the intact 2-iodoaryl group is transferred via presumed transition state TS1, which leads to a good AE (50% for 22a) and allows the further transformation of the α-arylation product 22 via cross coupling reactions. In addition, the in situ generation of the PIFA reagent proved viable, in order to
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Published 30 May 2018

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

  • Anna Czarnecka,
  • Emilia Kowalska,
  • Agnieszka Bodzioch,
  • Joanna Skalik,
  • Marek Koprowski,
  • Krzysztof Owsianik and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

Graphical Abstract
  • ) has been performed. It is important for the sulfur-containing substrates for which metal-catalyzed cross-coupling reactions fail. The dibenzylic OH group has been preferentially reduced with the ZnI2/Na(CN)BH3 system in the presence of an ortho-dithioacetal moiety to give ortho-1,3-dithianylaryl(aryl
  • the key substrates for aromatic cyclodehydration, also known as the Bradsher reaction [15], which leads to fused, polycyclic aromatic hydrocarbons [16][17][18][19]. This type of reaction found applications in synthesis of organic, optoelectronic materials [20][21][22]. Metal-catalyzed cross-coupling
  • reactions (e.g., Suzuki–Miyaura, Stille, Kumada, Hiyama or Negishi couplings) play a key role in the preparation of diarylmethanes. However, the reactions involving sulfur-containing moieties have not been reported yet (Scheme 1) [1]. It is noteworthy that under certain conditions, the Pd-catalyzed cross
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Published 29 May 2018

The first Pd-catalyzed Buchwald–Hartwig aminations at C-2 or C-4 in the estrone series

  • Ildikó Bacsa,
  • Dávid Szemerédi,
  • János Wölfling,
  • Gyula Schneider,
  • Lilla Fekete and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 998–1003, doi:10.3762/bjoc.14.85

Graphical Abstract
  • derivatives, bearing a lipophilic phenyl group attached to C-2 through an amino linker. In continuation of our studies with respect to cross-coupling reactions on ring A of 13α-estrone, here we disclose the development of a Pd-catalyzed C(sp2)–N coupling methodology for the transformation of 2-bromo- and 4
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Published 04 May 2018

Bromide-assisted chemoselective Heck reaction of 3-bromoindazoles under high-speed ball-milling conditions: synthesis of axitinib

  • Jingbo Yu,
  • Zikun Hong,
  • Xinjie Yang,
  • Yu Jiang,
  • Zhijiang Jiang and
  • Weike Su

Beilstein J. Org. Chem. 2018, 14, 786–795, doi:10.3762/bjoc.14.66

Graphical Abstract
  • [33][34] and axitinib [35][36][37][38] (Scheme 1). Mechanochemistry as a burgeoning technique to promote solvent-free reactions has led to remarkable advances [39][40][41][42], particularly for cross-coupling reactions [43][44][45], involving Heck coupling with the aid of stoichiometric amounts of
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Published 06 Apr 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

Graphical Abstract
  • better yields and easier catalyst recover [26] than traditional processes. Lipshutz and co-workers have successfully exploited micelles not only as nanoreactors, but as an outstanding platform for achieving greener organic reactions [26][65][66]. They have shown, for example, C–N cross-coupling reactions
  • -coupling reactions. Catalytic activity was compared to the activity of the freshly prepared free catalyst, and the palladium entrapment did not affect either the conversion or the yields of the reaction [28]. The catalyst immobilization also allowed facile Pd removal from the final product and catalyst
  • hydrophobic membrane and as a consequence a higher reaction rate. Dergunov et al. reported on the design of a porous polymeric nanoreactor with a lipid bilayer for coupling reactions [87]. These nanocapsules were loaded with palladium catalysts and successfully used in Suzuki, Sonogashira and Heck cross
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Published 29 Mar 2018

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

  • Katharina Hiebler,
  • Georg J. Lichtenegger,
  • Manuel C. Maier,
  • Eun Sung Park,
  • Renie Gonzales-Groom,
  • Bernard P. Binks and
  • Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

Graphical Abstract
  • development of heterogeneous Pd catalysts that are ready to be used in combination with biocatalysts for catalytic cascade synthesis of active pharmaceutical ingredients (APIs). In particular, we focus on the application of the catalytic systems for Suzuki–Miyaura cross-coupling reactions, which is the key
  • minimal leaching behaviour is demonstrated with various Suzuki–Miyaura cross-coupling reactions in batch as well as in continuous flow employing the so-called “plug & play reactor”. Finally, we demonstrate the use of these particles as the sole emulsifier of oil–water emulsions for a range of oils
  • , Pd-catalysed C–C cross-coupling reactions have become indispensable in many modern synthetic protocols both in the laboratory and on an industrial scale. A highly important representative of this class of transformation is the Suzuki–Miyaura reaction [5][6], involving the coupling of aryl halides
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Published 19 Mar 2018

Synthesis and stability of strongly acidic benzamide derivatives

  • Frederik Diness,
  • Niels J. Bjerrum and
  • Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

Graphical Abstract
  • fluorine) may be generated in good yields and further functionalized through nucleophilic aromatic substitution or cross-coupling reactions. It was found that the products were stable in dilute aqueous solutions, but they slowly hydrolyzed in concentrated solutions or in the presence of other strong acids
  • . SNAr reactions of fluoro-substituted benzamide derivatives. Cross-coupling reactions of N-triflylbenzoic acid derivatives. Hydrolysis rates of the 4-bromobenzoic acid derivatives. Supporting Information Supporting Information File 42: NMR spectra of synthesized compounds. Acknowledgements The Danish
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Published 27 Feb 2018

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills

  • Zi Liu,
  • Hui Xu and
  • Guan-Wu Wang

Beilstein J. Org. Chem. 2018, 14, 430–435, doi:10.3762/bjoc.14.31

Graphical Abstract
  • construction of C–X bonds. With the development of transition-metal-catalyzed cross-coupling reactions, a series of halogenations at the ortho-position of the directing groups have been disclosed [5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Nevertheless, from the viewpoint of green chemistry, the
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Published 16 Feb 2018

Recent developments in the asymmetric Reformatsky-type reaction

  • Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21

Graphical Abstract
  • ][8][9][10][11][12][13]. Moreover in 2014, two book chapters dealing with organozinc reagents were published covering the literature up to 2011 [14][15], and a review focusing on general SmI2-mediated cross-coupling reactions including only two references dated of 2013 concerning diastereoselective
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Published 02 Feb 2018

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 Suzuki–Miyaura 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
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Published 26 Jan 2018

Development of a fluorogenic small substrate for dipeptidyl peptidase-4

  • Futa Ogawa,
  • Masanori Takeda,
  • Kanae Miyanaga,
  • Keita Tani,
  • Ryuji Yamazawa,
  • Kiyoshi Ito,
  • Atsushi Tarui,
  • Kazuyuki Sato and
  • Masaaki Omote

Beilstein J. Org. Chem. 2017, 13, 2690–2697, doi:10.3762/bjoc.13.267

Graphical Abstract
  • groups. The data in Table 1 show that Hiyama cross-coupling reactions gave the desired TFPE-anilines and TFPE-phenylenediamines (1–4) in moderate to good yields. This method has the advantage that complete substitution of diiodo- and triiodoarenes can proceed to give disubstituted (1 and 3) and
  • on addition of DPP-4. Use of 1 as fluorogenic probe for DPP-4 activity. Synthesis of fluorogenic probe H-Gly-Pro-1. Synthesis of TFPE-anilines 1–4 via Hiyama cross-coupling reactions of iodoanilines with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane.a UV–vis absorption and fluorescence data for 1–4
  • fluorophore structure. This suggests that substitution with TFPE would be a reasonable approach to producing new fluorescent molecules. However, there are few methods for synthesizing TFPE-substituted compounds. In a previous study, we achieved the facile introduction of TFPE groups via Hiyama cross-coupling
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Published 14 Dec 2017

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

  • Matthias Wünsch,
  • David Schröder,
  • Tanja Fröhr,
  • Lisa Teichmann,
  • Sebastian Hedwig,
  • Nils Janson,
  • Clara Belu,
  • Jasmin Simon,
  • Shari Heidemeyer,
  • Philipp Holtkamp,
  • Jens Rudlof,
  • Lennard Klemme,
  • Alessa Hinzmann,
  • Beate Neumann,
  • Hans-Georg Stammler and
  • Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

Graphical Abstract
  • ], gold-catalyzed azetidin-3-one formation [16], as well as various transition metal-mediated additions and cross-coupling reactions [17] represent further important reactions of propargylamines, providing the potential to form innovative peptidomimetics (Figure 2). Our attention has been focused on the
  • , forming the scaffold of versatile peptidomimetics 11. According to the proposed rearrangement of alkyne 7 (Figure 9), the choice of base is crucial for such cross-coupling reactions. To get a better understanding of the reactivity of propargylamines, the stability and propensity for base induced
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Published 15 Nov 2017

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

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  • Engineering, Czestochowa University of Technology, Armii Krajowej 17, Czestochowa, 42-200, Poland 10.3762/bjoc.13.235 Abstract Nine new quadrupolar chromophores based on diketopyrrolopyrrole were designed and prepared by cross-coupling reactions. The property tuning has been achieved by structural variation
  • and its final cross-coupling reactions (Scheme 1). The construction of the DPP central scaffold 6 was accomplished by a well-known reaction between thiophene-2-carbonitrile and dimethyl succinate in the presence of sodium tert-amylalcoholate generated in situ [32]. The reaction provided 6 with a high
  • 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 Suzuki–Miyaura and Migita–Stille reactions leading to chromophores 1a–3a and 4a
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Published 08 Nov 2017

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

  • Satoru Mori and
  • Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

Graphical Abstract
  • ][91] or a peptide [92]. For example, TFEO-Pcs conjugated with peptides (15) have been reported [93]. A3B type TFEO-Pc was successfully condensed with peptides by palladium-catalyzed cross-coupling reactions in good yield (Scheme 5). These TFEO-Pc-peptide conjugates, which show a sharp Q band in the UV
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Published 27 Oct 2017

Synthesis of substituted Z-styrenes by Hiyama-type coupling of oxasilacycloalkenes: application to the synthesis of a 1-benzoxocane

  • James R. Vyvyan,
  • Courtney A. Engles,
  • Scott L. Bray,
  • Erik D. Wold,
  • Christopher L. Porter and
  • Mikhail O. Konev

Beilstein J. Org. Chem. 2017, 13, 2122–2127, doi:10.3762/bjoc.13.209

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  • James R. Vyvyan Courtney A. Engles Scott L. Bray Erik D. Wold Christopher L. Porter Mikhail O. Konev Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225, USA 10.3762/bjoc.13.209 Abstract Several Hiyama cross-coupling reactions of oxasilacycloalkenes and
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Published 11 Oct 2017

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

  • Debasish Sengupta,
  • Koushik Bhowmik,
  • Goutam De and
  • Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

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  • catalyst. It is observed that the uniformly dispersed Ni NPs supported on RGO could exhibit excellent catalytic activity in C–S cross-coupling reactions and the catalytic application is generalized with diverse coupling partners. Although the electron-rich planar RGO surface helps in stabilizing the
  • first palladium-catalyzed arylation of thiols was reported by Migita and co-workers in 1980 [5], and soon after Cristau and co-workers developed a nickel-catalyzed route for C–S cross-coupling reactions [6]. Other metals such as copper [7], cobalt [8], iron [9], rhodium [10], manganese [11], indium [12
  • properties [14]. The Ni-catalyzed C–S cross-coupling reactions generally involved Ni salts [15][16][17][18], Ni–phosphine complexes [19][20][21], or Ni–NHC complexes [22][23], although the actual catalyst is believed to be a Ni(0)/Ni(I) species [16][17][18][19][20][21]. NiO supported on zirconia (NiO–ZrO2
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Published 28 Aug 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
  • -catalyzed cross-coupling reactions to form C–C bonds are very powerful synthetic tools in modern organic synthesis [7]. With their increasing applications in the synthesis of pharmaceuticals, natural products and functional materials [8][9][10], moving these useful transformations to occurring in aqueous
  • media became more and more attractive [11]. Despite there are several strategies for palladium-catalyzed cross-coupling reactions in water, such as microwave heating [12], ultrasonic irradiation [13][14] and ligand-free methodology [15][16], the more efficient and preferable one is the use of water
  • ligands, functionalized with sulfonate- [41][42][43][44][45][46], carboxylate- [47][48][49][50][51][52], polyether- [53][54][55][56][57][58][59] and other hydrophilic groups [60][61][62][63], have been developed and used in the aqueous Pd-catalyzed cross-coupling reactions. Among them, most of them were
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Published 21 Aug 2017

Encaging palladium(0) in layered double hydroxide: A sustainable catalyst for solvent-free and ligand-free Heck reaction in a ball mill

  • Wei Shi,
  • Jingbo Yu,
  • Zhijiang Jiang,
  • Qiaoling Shao and
  • Weike Su

Beilstein J. Org. Chem. 2017, 13, 1661–1668, doi:10.3762/bjoc.13.160

Graphical Abstract
  • easily recovered and reused for at least five times without significant loss of catalytic activity. Keywords: ball milling; Heck reaction; layer double hydroxides; solvent-free; supported Pd catalyst; Introduction High-speed ball milling (HSBM)-assisted transition metal-catalyzed cross-coupling reactions
  • %), TBAB (1.5 mmol), K2CO3 (3.6 mmol), and silica gel 5 g were placed in a 80 mL stainless-steel vessel (ΦMB = 0.25, dMB = 5 mm). HSBM conditions: 60 min at 800 rpm. Supported catalysts in cross-coupling reactions. MM represents mixer mill; PM represents planetary mill. Selected model reaction. Pd/MgAl
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Published 14 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

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  • ], published in 2007, Kishi and co-workers increased the overall efficiency of the synthesis by reorganizing the assembly of the principal fragments and by optimizing the key C(sp2)–C(sp3) Negishi cross-coupling reactions as well as the choice of protecting groups. The 3rd generation approach [123], published
  • mycolactone core structure is depicted in Scheme 1. It relied on two consecutive Negishi cross-coupling reactions [124] to construct the linear C1–C20 fragment, which was to be cyclized by macrolactonization [39]. Vinyl iodide 19, corresponding to the C14–C20 part of the core extension, was synthesized from
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Published 11 Aug 2017

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

  • Benedikt C. Melzer and
  • Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

Graphical Abstract
  • species with ZnCl2 should lead to at C-1 zincated isoquinolines, which could undergo Negishi cross-coupling reactions with appropriately substituted methyl 2-bromobenzoates to give methyl 2-(isoquinolin-1-yl)benzoates. These would again open an access to oxoisoaporphine alkaloids via intramolecular
  • , which were expected to be versatile substrates for Suzuki cross-coupling reactions with appropriate phenylboronic acids to gain methyl 2-(isoquinolin-1-yl)benzoates as the central intermediates (Scheme 1). Results and Discussion As we reported previously, metalation of 6,7-dimethoxyisoquinoline (7a) and
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Published 08 Aug 2017
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