Search results

Search for "homocoupling" in Full Text gives 72 result(s) in Beilstein Journal of Organic Chemistry.

Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations

  • Fatiha Abdelmalek,
  • Fazia Derridj,
  • Safia Djebbar,
  • Jean-François Soulé and
  • Henri Doucet

Beilstein J. Org. Chem. 2015, 11, 2012–2020, doi:10.3762/bjoc.11.218

Graphical Abstract
  • . We were pleased to find that only one regioisomer was formed, as the arylation exclusively occurred at the C–H bond between fluorine and chlorine atoms. The desired (hetero)aryl triad 31 was isolated in moderate yield, due to the formation of a relatively large amount of homocoupling product of the
PDF
Album
Supp Info
Full Research Paper
Published 28 Oct 2015

[2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties

  • Laura G. Sarbu,
  • Lucian G. Bahrin,
  • Peter G. Jones,
  • Lucian M. Birsa and
  • Henning Hopf

Beilstein J. Org. Chem. 2015, 11, 1917–1921, doi:10.3762/bjoc.11.207

Graphical Abstract
  • involves the conversion of 2-N,N-dialkylamino-1,3-dithiolium salts into the corresponding 2-unsubstituted 1,3-dithiolium salts, followed by the homocoupling of the carbene intermediate that is generated under basic conditions. Unfortunately, our attempts to synthesize the 2-unsubstituted derivative from
PDF
Album
Supp Info
Letter
Published 15 Oct 2015

Asymmetric 1,4-bis(ethynyl)bicyclo[2.2.2]octane rotators via monocarbinol functionalization. Ready access to polyrotors

  • Cyprien Lemouchi and
  • Patrick Batail

Beilstein J. Org. Chem. 2015, 11, 1881–1885, doi:10.3762/bjoc.11.202

Graphical Abstract
  • homocoupling [19] of the mono-terminated alkene BCOs 1, 5 and 8, respectively (Scheme 2). Note that the scope of our earlier synthesis was much narrower since it only allows the preparation of a monopyridine derivative, 5 subsequently engaged to yield 6 and could not be upscaled to produce the targets in gram
  • solubility considerations, as it enhances the reactivity in the homocoupling reaction and also facilitates the purification of 9 by chromatography on silica gel. This yielded the dicarboxylate diyne dirotor 10 with the high purity required for the preparation of framework solids. Saponification of the ester
PDF
Album
Supp Info
Full Research Paper
Published 09 Oct 2015

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

  • George Iakobson,
  • Junyi Du,
  • Alexandra M. Z. Slawin and
  • Petr Beier

Beilstein J. Org. Chem. 2015, 11, 1494–1502, doi:10.3762/bjoc.11.162

Graphical Abstract
  • -coupling reactions with varied degree of success. The most efficient cross-coupling reactions were the Heck reactions with alkenes, a biaryl homocoupling reaction, an azo coupling to electron-rich arenes, and a dediazoniation with TMSN3 in an ionic liquid medium [74][75]. An efficient borylation of
PDF
Album
Supp Info
Full Research Paper
Published 26 Aug 2015

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

  • Rupert G. D. Taylor,
  • Joseph Cameron,
  • Iain A. Wright,
  • Neil Thomson,
  • Olena Avramchenko,
  • Alexander L. Kanibolotsky,
  • Anto R. Inigo,
  • Tell Tuttle and
  • Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

Graphical Abstract
  • constructing a half-unit functionalised with a 1,3-dithiol-2-one, that can undergo a triethyl phosphite-mediated homocoupling to synthesise the central dithienoTTF in the final step. Herein, we present an alternative divergent route to dithienoTTFs, by utilising 4,6,4’,6’-tetrabromo-[2,2’]bis(thieno[3,4-d][1,3
  • ]dithiolylidene) [15] as a core and appending heterocyclic arms through microwave assisted Stille couplings. It is worth noting that the tetrabromo-dithienoTTF core is still prepared via a triethyl phosphite-mediated homocoupling, but in this divergent route valuable heterocyclic groups can be introduced at the
PDF
Album
Supp Info
Full Research Paper
Published 10 Jul 2015

Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes

  • Luke J. O’Driscoll,
  • Sissel S. Andersen,
  • Marta V. Solano,
  • Dan Bendixen,
  • Morten Jensen,
  • Troels Duedal,
  • Jess Lycoops,
  • Cornelia van der Pol,
  • Rebecca E. Sørensen,
  • Karina R. Larsen,
  • Kenneth Myntman,
  • Christian Henriksen,
  • Stinne W. Hansen and
  • Jan O. Jeppesen

Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125

Graphical Abstract
  • prepare BPTTFs using homocoupling reactions and functionalised MPTTFs using cross-coupling reactions with a variety of 1,3-dithiole-2-thiones (19). Subsequently, the incorporation of more complex functionality is discussed. We show how the 2-cyanoethyl protecting group can be used to afford MPTTFs
  • derivatives can be prepared from 6 and 7 by means of coupling reactions in triethyl phosphite (Scheme 3). The known homocoupling reaction of 6 affords the bis-tosylated BPTTF 5a in high yield with minimal purification [25]. We have obtained a comparable yield (76% vs 84%) working at twice the previously
  • MPTTFs using homocoupling reactions or cross-coupling reactions with 1,3-dithiole-2-thiones (19), respectively. Additional functionalisation of MPTTFs and BPTTFs is important to allow their incorporation into systems with materials applications. The use of the 2-cyanoethyl protecting group allows
PDF
Album
Supp Info
Full Research Paper
Published 03 Jul 2015

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

  • Sandrina Oliveira,
  • Dulce Belo,
  • Isabel C. Santos,
  • Sandra Rabaça and
  • Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

Graphical Abstract
  • pure triethyl phosphite during 4 hours at 130 °C leading to the formation of 3 in relatively high yield (63%) (Scheme 1). This coupling reaction also gives rise to smaller amounts of BEDT-TTF (14% yield) and dicyanodibenzene tetrathiafulvalene (dcdb-TTF) [13] as byproducts resulting from homocoupling
PDF
Album
Supp Info
Letter
Published 03 Jun 2015

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

Graphical Abstract
  • afforded molecular hydrogen and unsymmetrical ester 187 (Scheme 39) [182]. Cross-coupling products 187 were obtained in high yields; the expected homocoupling of primary alcohols giving symmetrical esters and the dehydrogenation of secondary alcohols yielding ketones were avoided. 3 Ketones and 1,3
PDF
Album
Review
Published 20 Jan 2015

An improved procedure for the preparation of Ru(bpz)3(PF6)2 via a high-yielding synthesis of 2,2’-bipyrazine

  • Danielle M. Schultz,
  • James W. Sawicki and
  • Tehshik P. Yoon

Beilstein J. Org. Chem. 2015, 11, 61–65, doi:10.3762/bjoc.11.9

Graphical Abstract
  • equiv of isopropanol, and 1.5 equiv of K2CO3 in DMF (0.4 M) at 100 °C; under these conditions, the reaction was complete in 2 h and afforded the desired homocoupling product in 81% isolated yield (Table 1, entry 9). Although our investigations were motivated by our specific need to access photocatalyst
  • synthesis of the strongly oxidizing photocatalyst Ru(bpz)3(PF6)2 [39]. Influence of ligand structure on photoredox behavior. Pd-catalyzed reductive coupling of 2-chloropyrazine. Preparative-scale synthesis of Ru(bpz)3(PF6)2. Optimization of Pd-catalyzed reductive homocoupling of 2-halopyrazines.a Pd
PDF
Album
Supp Info
Letter
Published 14 Jan 2015

Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach

  • Martin C. N. Brauer,
  • Ricardo A. W. Neves Filho,
  • Bernhard Westermann,
  • Ramona Heinke and
  • Ludger A. Wessjohann

Beilstein J. Org. Chem. 2015, 11, 25–30, doi:10.3762/bjoc.11.4

Graphical Abstract
  • synthesized through an Ugi four-component reaction (U-4CR) followed by a copper-catalysed alkyne homocoupling (Glaser reaction). The short and chemoselective reaction sequence allows generating diverse (pseudo) dimeric peptoids. A combinatorial version allows the one-pot preparation of, e.g., six-compound
  • increasing interest to synthesize dimerized peptidomimetics with pharmacological properties through a step-efficient protocol that allows rapid access to highly diverse dimer libraries, we set out to develop a strategy based on an U-4CR/Glaser-type homocoupling sequence [34]. In comparison to popular cross
  • were obtained in good yields. The next step was the copper-catalysed homocoupling (Glaser reaction) of the terminal alkyne functions. Albeit several protocols are reported for this reaction, the CuCl-catalyzed method recently described by Jia and co-workers was utilised to access the C2-symmetric 1,3
PDF
Album
Supp Info
Video
Full Research Paper
Published 07 Jan 2015

Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing

  • Bradley D. Rose,
  • Peter J. Santa Maria,
  • Aaron G. Fix,
  • Chris L. Vonnegut,
  • Lev N. Zakharov,
  • Sean R. Parkin and
  • Michael M. Haley

Beilstein J. Org. Chem. 2014, 10, 2122–2130, doi:10.3762/bjoc.10.219

Graphical Abstract
  • transannular cyclization of 10 using elemental iodine under air [21]. Dehydrobenzo[12]annulene 10 in turn was synthesized via Glaser homocoupling of 1,2-diethynylbenzene [21][22][23]. While in theory this route permitted relatively easy access to diethynyldiones 8, in practice it was fraught with problems: (1
PDF
Album
Supp Info
Full Research Paper
Published 05 Sep 2014

Synthesis of rigid p-terphenyl-linked carbohydrate mimetics

  • Maja Kandziora and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182

Graphical Abstract
  • to heat, air and moisture compared to other organometallic reagents [21]. Up to now there are not many examples of nanorod-like carbohydrate dimers with aryl-linked divalent glycosides. A mannopyranoside dimer was generated by a palladium-catalyzed Ullmann-type reductive homocoupling [22] and
PDF
Album
Supp Info
Full Research Paper
Published 30 Jul 2014

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

  • Fabian Klukas,
  • Alexander Grunwald,
  • Franziska Menschel and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

Graphical Abstract
  • ]. However, the major drawback of this approach is the complex, time-consuming preparation of the complicated gold catalyst and the separate synthesis of the butadiyne substrates. In a similar study arylbutadiynes prepared by Glaser homocoupling were converted into symmetrical 2,5-di(hetero)arylfurans [32
PDF
Album
Supp Info
Full Research Paper
Published 18 Mar 2014

Silver and gold-catalyzed multicomponent reactions

  • Giorgio Abbiati and
  • Elisabetta Rossi

Beilstein J. Org. Chem. 2014, 10, 481–513, doi:10.3762/bjoc.10.46

Graphical Abstract
PDF
Album
Review
Published 26 Feb 2014

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

  • Regina Berg and
  • Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

Graphical Abstract
  • )4][PF6]. However, acetonitrile as co-solvent and the presence of a nitrogen base such as triethylamine, N,N-diisopropylethylamine (DIPEA) or pyridine are required for these catalyses to work. Sharpless also reports the formation of diacetylenes by alkyne homocoupling as well as bistriazoles and 5
PDF
Album
Review
Published 02 Dec 2013

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

  • Gianluigi Broggini,
  • Egle M. Beccalli,
  • Andrea Fasana and
  • Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

Graphical Abstract
  • . This N-(2-pyridyl)sulfonyl-directing strategy has also been extended to the development of a protocol for the intermolecular, dehydrogenative homocoupling of indole, providing 2,2’-bisindoles 7. Intermolecular Pd(II)-catalyzed N–H functionalization has also been successfully used to achieve N
PDF
Album
Review
Published 11 Oct 2012

Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

  • Nora L. Löw,
  • Egor V. Dzyuba,
  • Boris Brusilowskij,
  • Lena Kaufmann,
  • Elisa Franzmann,
  • Wolfgang Maison,
  • Emily Brandt,
  • Daniel Aicher,
  • Arno Wiehe and
  • Christoph A. Schalley

Beilstein J. Org. Chem. 2012, 8, 234–245, doi:10.3762/bjoc.8.24

Graphical Abstract
  • gave the di- and tritopic axles 17–19 and 21 in DMF/NEt3 with decent yields when the temperature was raised to 70 °C. The copper-free Sonogashira procedure was again applied for the synthesis of tetravalent guest 23 (Scheme 6) and yielded 17% of the product. Interestingly, a homocoupling of axle 2 gave
PDF
Album
Supp Info
Full Research Paper
Published 09 Feb 2012

Impact of the level of complexity in self-sorting: Fabrication of a supramolecular scalene triangle

  • Kingsuk Mahata and
  • Michael Schmittel

Beilstein J. Org. Chem. 2011, 7, 1555–1561, doi:10.3762/bjoc.7.183

Graphical Abstract
  • ] (Figure 1). The coordination behaviour of molecular component 3 was integrated into 5, the latter being synthesised in a Sonogashira homocoupling reaction [27]. The information stored in 1 and 4 was instated in the unsymmetrical bisphenanthroline 6, readily accessible by stepwise Sonogashira cross
PDF
Album
Supp Info
Letter
Published 22 Nov 2011

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

  • Paul Knochel,
  • Matthias A. Schade,
  • Sebastian Bernhardt,
  • Georg Manolikakes,
  • Albrecht Metzger,
  • Fabian M. Piller,
  • Christoph J. Rohbogner and
  • Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

Graphical Abstract
  • (Scheme 5) [13][14]. A broad range of functional groups are tolerated, and homocoupling products account for less than 5% of the total. These benzylic zinc reagents give access to biologically important phenylacetic acids. Thus, the treatment of the chloro-substituted benzylic zinc compound 28 with
PDF
Album
Supp Info
Review
Published 13 Sep 2011

Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling

  • Aiichiro Nagaki,
  • Yuki Uesugi,
  • Yutaka Tomida and
  • Jun-ichi Yoshida

Beilstein J. Org. Chem. 2011, 7, 1064–1069, doi:10.3762/bjoc.7.122

Graphical Abstract
  • homocoupling of aryllithiums, and this enabled its integration with the halogen–lithium exchange reaction of aryl halides in a flow microreactor. This system allows the homocoupling of two aryl halides bearing electrophilic functional groups, such as CN and NO2, in under a minute. Keywords: homocoupling; iron
  • salts; microreactor; organolithiums; Introduction Biaryl structures often occur in various organic compounds including natural products, bioactive compounds, functional polymers, ligands in catalysts and theoretically interesting molecules, and the oxidative homocoupling of arylmetals is one of the
  • most useful methods for the construction of biaryl frameworks [1]. Stoichiometric amounts of transition metal salts such as TiCl4 [2], TlCl [3], VO(OEt)Cl2 [4], CoCl2 [5], CuCl2 [6] and Pd(OAc)2 [7] have been used for homocoupling of arylmetals. In some cases catalytic processes in the presence of a
PDF
Album
Supp Info
Full Research Paper
Published 02 Aug 2011

Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF2

  • Lukas J. Gooßen,
  • Bettina Zimmermann and
  • Thomas Knauber

Beilstein J. Org. Chem. 2010, 6, No. 43, doi:10.3762/bjoc.6.43

Graphical Abstract
  • protodecarboxylation could not effectively be suppressed (entry 12). Another unwanted byproduct, i.e. 2,2′-dinitrobiphenyl, appeared when reducing the quantity of the copper fluoride to less than 1 equivalent, which results from homocoupling of the arylcopper intermediate (entry 13). The selectivity for the vinyl
PDF
Album
Supp Info
Full Research Paper
Published 03 May 2010

Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions

  • Klaas Mennecke and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2009, 5, No. 21, doi:10.3762/bjoc.5.21

Graphical Abstract
  • partners. With n-butylamine as base and 2.5 mol% catalyst 3 in DMF at 120 °C and a flow rate of 2 mL/min it was possible to achieve full conversion with complete E-selectivity within 30 min. Formation of by-products resulting from homocoupling was not observed. When 4′-iodoacetophenone (23) was exchanged
PDF
Album
Supp Info
Full Research Paper
Published 08 May 2009
Other Beilstein-Institut Open Science Activities