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Search for "aryl iodides" in Full Text gives 110 result(s) in Beilstein Journal of Organic Chemistry.

A novel 4-aminoantipyrine-Pd(II) complex catalyzes Suzuki–Miyaura cross-coupling reactions of aryl halides

  • Claudia A. Contreras-Celedón,
  • Darío Mendoza-Rayo,
  • José A. Rincón-Medina and
  • Luis Chacón-García

Beilstein J. Org. Chem. 2014, 10, 2821–2826, doi:10.3762/bjoc.10.299

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  • 58030, tel.: +52 443 326 5790; fax: +52 443 326 5788 10.3762/bjoc.10.299 Abstract A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under
  • scope of the SM cross-coupling reaction using the 4-AAP–Pd(II) complex, we examined the reactions of a wide array of electronically diverse aryl iodides and bromides with electron-withdrawing or electron-donating substituents on the phenylboronic acids. The effects of the substituents of the arylboronic
  • tolerant for both electron-donating and electron-withdrawing substituents; our protocol successfully accommodated the free hydroxy and amino groups as substituents on the aryl iodides and bromides without additional protection procedures, and the reactions with these substrates produced the corresponding
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Published 01 Dec 2014

Multicomponent reactions in nucleoside chemistry

  • Mariola Koszytkowska-Stawińska and
  • Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

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  • the addition of the nucleoside moiety to the C-1 or C-2 carbon atom of the C=C double bond. The three-component reactions of nucleoside-derived (uridine or thymidine) allenes 97, a range of aryl iodides, and 1-adamantylamine was accomplished smoothly under the palladium-catalyzed conditions (Scheme 40
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Published 29 Jul 2014

Preparation of phosphines through C–P bond formation

  • Iris Wauters,
  • Wouter Debrouwer and
  • Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

Graphical Abstract
  • reactions of secondary phosphines with several electrophiles, including alkyl halides (alkylation), alkenes (hydrophosphination) and aryl iodides (arylation). Chan et al. synthesized P-stereogenic phosphine boranes using a ruthenium catalyst. The secondary phosphine 36a underwent an enantioselective
  • preferred over tristannyl derivatives since they are less toxic. However, in recent years the group of Rossi has reported a one-pot procedure for the palladium-catalyzed coupling of aryl iodides 97 with in situ generated Ph2SnBu3 (30, Scheme 27) [170]. When naphthyl triflate was used as a substrate, CuI was
  • -catalyzed phosphination of aryl triflates and nonaflates instead of aryl iodides with phosphine boranes [158]. The first examination towards an enantioselective C–P cross-coupling starting from racemic secondary phosphine boranes was performed by Gaumont and Pican [175]. The highest enantiomeric excess
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Published 09 May 2014

Phosphinate-containing heterocycles: A mini-review

  • Olivier Berger and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2014, 10, 732–740, doi:10.3762/bjoc.10.67

Graphical Abstract
  • [23][36]. This versatile intermediate 59 was reacted with aldehydes, imines, olefins and aryl bromides or aryl iodides to generate a wide range of phosphinates. The same authors have also prepared another H-phosphinate intermediate 61 in 71% yield (Scheme 25) [37]. This oxazaphosphinane 61 was
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Published 27 Mar 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

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  • approach are clearly the extended reaction times (3–6 d) and the removal of the catalyst after the coupling step. Recently, we became particularly interested in sequentially Pd-catalyzed processes [35] starting from (hetero)aryl iodides [36]. In particular, the Pd–Cu-catalyzed Sonogashira–Glaser sequence
  • proved to be beneficial (Table 1, entries 10–13). The optimal conditions for this cyclization are marked in entry 12 of Table 1. With these optimized conditions in hand we started to concatenate the one-pot sequence by generating the required 1,4-butadiynes from (hetero)aryl iodides. First, the
  • solvent. Finally, starting from (hetero)aryl iodides 3 and TMSA we combined the Sonogashira–Glaser sequence with the cyclization step into a one-pot sequence and studied the substrate scope of this pseudo five-component synthesis of 2,5-di(hetero)arylfurans 2 (Scheme 2). All reactions were performed on a
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Published 18 Mar 2014

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

  • Phei Li Lau,
  • Ray W. K. Allen and
  • Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

Graphical Abstract
  • been reported by numerous authors. Among them, Zhao et al. [18] studied the coupling of non-activated aryl iodides with different alkenes using Pd-MCM-41-NH2. Other examples include Pd-FSM 16 (functionalised with pyridine-carboimine or quinoline-carboimine) [19], oxime carbapalladacycle anchored on
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Published 17 Dec 2013

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

Graphical Abstract
  • monofluoromethylation was described by J. Hu. Aryl iodides were submitted to a Cu-catalyzed (CuTC = copper thiophene-2-carboxylate) debenzoylative fluoroalkylation with 2-PySO2CHFCOR followed by desulfonylation (Scheme 2) [49]. It has been shown that the (2-pyridyl)sulfonyl moiety is important for the Cu-catalysis. 2
  • been reported. H. Amii reported on the reaction of aryl iodides with α-silyldifluoroacetates in the presence of a catalytic amount of CuI (Scheme 3). The corresponding aryldifluoroacetates have been obtained in moderate to good yields and afforded, after subsequent hydrolysis of the
  • trifluoromethylation of aryl iodides with TESCF3 in presence of potassium fluoride [33]. After activation of the fluoroalkylsilane by the fluoride, the trifluoromethyl anion is generated and leads to the formation of the CF3Cu species. Then, σ-bond metathesis between Ar–I and CF3–Cu yields trifluoromethylated arenes
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Published 15 Nov 2013

Consecutive cross-coupling reactions of 2,2-difluoro-1-iodoethenyl tosylate with boronic acids: efficient synthesis of 1,1-diaryl-2,2-difluoroethenes

  • Ju Hee Kim,
  • Su Jeong Choi and
  • In Howa Jeong

Beilstein J. Org. Chem. 2013, 9, 2470–2475, doi:10.3762/bjoc.9.286

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  • the consecutive cross-coupling reaction of the 2,2-difluoro-1-bromoethenylzinc reagent with aryl iodides, followed by arylboronic acids [17]. Recently, we also prepared 2,2-difluoro-1-tributylstannylethenyl tosylate and (2,2-difluoroethenylidene)bis(tributylstannane) which were utilized in the
  • palladium-catalyzed consecutive cross-coupling reactions with electrophilic aryl iodides or nucleophilic arylstannane reagents to afford the corresponding 1,1-diaryl-2,2-difluoroethenes [20][21]. However, these previous reagents still have some drawbacks such as the existence of the toxic tributylstannyl
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Published 14 Nov 2013

Microwave-assisted synthesis of 5,6-dihydroindolo[1,2-a]quinoxaline derivatives through copper-catalyzed intramolecular N-arylation

  • Fei Zhao,
  • Lei Zhang,
  • Hailong Liu,
  • Shengbin Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2013, 9, 2463–2469, doi:10.3762/bjoc.9.285

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  • proceeded smoothly with high yields for substrates with electron deficient aryl iodides, whereas methyl-substituted substrate 2l required additional 15 minutes to complete the transformation (Table 2, entries 9–12). This indicated that electron-deficient aryl iodides display a better reactivity than
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Published 14 Nov 2013

Oxidative 3,3,3-trifluoropropylation of arylaldehydes

  • Akari Ikeda,
  • Masaaki Omote,
  • Shiho Nomura,
  • Miyuu Tanaka,
  • Atsushi Tarui,
  • Kazuyuki Sato and
  • Akira Ando

Beilstein J. Org. Chem. 2013, 9, 2417–2421, doi:10.3762/bjoc.9.279

Graphical Abstract
  • aldehydes in the presence of fluoride anion [29]. Recently, Prakash et al. [30] reported the synthesis of β-trifluoromethylstyrenes through a Heck coupling reaction of aryl iodides with 1-iodo-3,3,3-trifluoropropane, allowing a direct introduction of 3,3,3-trifluoropropenyl groups to aromatic rings
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Published 11 Nov 2013

Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide

  • Yuzo Nakamura,
  • Motohiro Fujiu,
  • Tatsuya Murase,
  • Yoshimitsu Itoh,
  • Hiroki Serizawa,
  • Kohsuke Aikawa and
  • Koichi Mikami

Beilstein J. Org. Chem. 2013, 9, 2404–2409, doi:10.3762/bjoc.9.277

Graphical Abstract
  • The trifluoromethylation of aryl iodides catalyzed by copper(I) salt with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide and Zn dust was accomplished. The catalytic reactions proceeded under mild reaction conditions, providing the corresponding aromatic trifluoromethylated
  • solid, can also be used for the trifluoromethylation of aryl iodides, while stoichiometric amounts of copper(I) bromide are required to afford the more reactive trifluoromethyl copper (CuCF3) species by transmetallation [13][14]. However, these reagents are generally prepared from trifluoromethyl
  • described above, much of the area of catalytic trifluoromethylations with trifluoromethylzinc reagent has not been explored yet, compared to the area of catalytic trifluoromethylations with the Ruppert–Prakash reagents [7][11][12][18][19][20][21]. Herein, we report the trifluoromethylations of aryl iodides
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Published 08 Nov 2013

Homolytic substitution at phosphorus for C–P bond formation in organic synthesis

  • Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 1269–1277, doi:10.3762/bjoc.9.143

Graphical Abstract
  • diphosphination of terminal alkynes. Photoinduced radical diphosphination with tetrafluorodiphosphine. Thiophosphination of terminal alkynes. Photoinduced thio- and selenophosphination by dichalcogen/diphosphine binary system. Radical phosphination of aryl iodides. Radical phosphination of alkyl imidazole-1
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Published 28 Jun 2013

Camera-enabled techniques for organic synthesis

  • Steven V. Ley,
  • Richard J. Ingham,
  • Matthew O’Brien and
  • Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

Graphical Abstract
  • directly in another synthetic step. For example, in a recent multistep flow synthesis of branched aldehydes from aryl iodides [98], an in-line aqueous extraction step following an ethylene-Heck reaction allowed the intermediate styrene products to be carried directly into a subsequent downstream
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Published 31 May 2013

Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C–H functionalization

  • Ryan Pearson,
  • Shuyu Zhang,
  • Gang He,
  • Nicola Edwards and
  • Gong Chen

Beilstein J. Org. Chem. 2013, 9, 891–899, doi:10.3762/bjoc.9.102

Graphical Abstract
  • excellent directing group for a range of Pd-catalyzed C–H functionalization reactions [26][27][28][29][30][31][32][33][34][35]. In 2005, the Daugulis laboratory first reported that the ortho-C(sp2)−H bond of benzylpicolinamides could be arylated with aryl iodides under Ag-promoted Pd-catalyzed conditions
  • determination of the scope of this reaction with benzylpicolinamide and aryl iodide substrates. With the optimized conditions in hand, we next explored the scope of benzylpicolinamide and aryl iodide substrates (Figure 1). The electronic properties of benzylpicolinamide and aryl iodides had little influence on
  • the reactivity, as benzylpicolinamide and aryl iodide substrates bearing electron-donating and withdrawing substituents react in good yields (3, 8, and 12). Significantly decreased arylation yield was observed for ortho-substituted aryl iodides (e.g., 9). The sterics of the benzylpicolinamides is also
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Published 08 May 2013

Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

  • Silvia M. Soria-Castro and
  • Alicia B. Peñéñory

Beilstein J. Org. Chem. 2013, 9, 467–475, doi:10.3762/bjoc.9.50

Graphical Abstract
  • of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under
  • the reactions of KSCOMe (1) with aryl iodides under a Cu/ligand/base-free system to afford S-aryl thioacetates 2 as thiol surrogates in good to excellent yields, under conventional heating and microwave irradiation as an efficient access to a variety of sulfur compounds. Results and Discussion
  • variety of commercially available aryl iodides were subjected to the optimized reaction conditions (Table 2, entry 1) to determine the scope of this catalytic system for the synthesis of S-aryl thioacetates 2, and the results are summarized in Table 3. As described in Table 3, the coupling of thioacetate
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Published 04 Mar 2013

N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides

  • Ismail Özdemir,
  • Nevin Gürbüz,
  • Nazan Kaloğlu,
  • Öznur Doğan,
  • Murat Kaloğlu,
  • Christian Bruneau and
  • Henri Doucet

Beilstein J. Org. Chem. 2013, 9, 303–312, doi:10.3762/bjoc.9.35

Graphical Abstract
  • imidazolylidene carbene ligands for the Pd-catalyzed direct arylation of pyrroles or indoles using bromobenzene and aryl iodides [42]. They observed that an important steric demand on the carbene ligand led to better results. Recently, the use of palladium(II) acetate complexes bearing both a phosphine and a
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Published 12 Feb 2013

Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles

  • Rajkumar Jeyachandran,
  • Harish Kumar Potukuchi and
  • Lutz Ackermann

Beilstein J. Org. Chem. 2012, 8, 1771–1777, doi:10.3762/bjoc.8.202

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  • mandatory. Indeed, our strategy turned out to be viable in a nonsequential manner by directly employing equimolar amounts of the three substrates. Hence, inexpensive CuI allowed the direct assembly of aryl iodides 1, alkyl bromides 2 and NaN3 with excellent chemo- and regioselectivities (Scheme 4). Thereby
  • - and step-economical access to annulated carbo- as well as O- and N-heterocycles. Finally, we found that the catalytic system also proved to be applicable to the one-pot copper-catalyzed direct arylation of various azoles 5 through N–H/C–H bond cleavages with aryl iodides 6 as the organic electrophiles
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Published 16 Oct 2012

Organocatalytic C–H activation reactions

  • Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

Graphical Abstract
  • the optimized conditions, different aryl iodides were tested and good to excellent yields (38–92%) were obtained [33]. Dihalobenzenes were also employed as substrates, and poor to good yields (29–79%) for the products 21 were observed (Scheme 14). However, the reaction failed with anisole and toluene
  • under the same reaction conditions. Shi and co-workers reported a similar reaction with 1,10-phenanthroline as catalyst at 100 °C employing aryl iodides and aryl bromides as the substrates [34]. Whereas 40 mol % of the catalyst and 3.0 equivalents of potassium tert-butoxide as base were needed for the
  • reaction with bromides, 20 mol % of the catalyst and 2.0 equivalents of potassium tert-butoxide were required for the reaction with iodides. Under these optimized conditions, different aryl bromides and aryl iodides were screened, and poor to good yields (27–89%) for the products 20 were observed (Scheme
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Published 27 Aug 2012

Hybrid super electron donors – preparation and reactivity

  • Jean Garnier,
  • Douglas W. Thomson,
  • Shengze Zhou,
  • Phillip I. Jolly,
  • Leonard E. A. Berlouis and
  • John A. Murphy

Beilstein J. Org. Chem. 2012, 8, 994–1002, doi:10.3762/bjoc.8.112

Graphical Abstract
  • ][23][24][25][26][27]. Benzimidazole-derived donor 1 converted aryl iodides to aryl radicals by transfer of a single electron at 110 °C [17], and was the first neutral organic ground-state molecule to achieve this. Later, the more powerful reagents 2 [18], 4 [20] and 5 [21] and related compounds [25
  • motif, 6, which marks a weaker donor. To extend the capabilities of such reagents, we now set out to design the first neutral, organic ground-state donor that could, at room temperature, reduce aryl iodides to aryl radicals (thereby acting as a single-electron donor) as opposed to aryl anions. Hybrid
  • by Ames et al. [15] demonstrate the same effect. This instability suggested that it should be difficult to obtain complete reaction when using 26 as a precursor of 10 in the preparative-scale reduction of aryl iodides. The standard two iodides 28 and 30 were tested under slightly different conditions
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Published 03 Jul 2012

Recent advances in direct C–H arylation: Methodology, selectivity and mechanism in oxazole series

  • Cécile Verrier,
  • Pierrik Lassalas,
  • Laure Théveau,
  • Guy Quéguiner,
  • François Trécourt,
  • Francis Marsais and
  • Christophe Hoarau

Beilstein J. Org. Chem. 2011, 7, 1584–1601, doi:10.3762/bjoc.7.187

Graphical Abstract
  • extended by Daugulis who reported a first general methodology for the Cu(I)-catalyzed direct arylation of heterocycles by using aryl iodides electrophiles and based upon the use of lithium tert-butoxide as a strong base [45]. In particular, monoarylation of oxazole occurred selectively at the C2 position
  • in 59% yield (Scheme 8). Miura subsequently disclosed the Cu(I)-catalyzed direct arylation of 5-arylated oxazoles with aryl iodides by employing triphenylphosphine ligand and sodium carbonate base (Scheme 8) [46]. Recently, You et al. reported convenient conditions for Cu(I)-catalyzed direct
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Published 29 Nov 2011

Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira–Glaser cyclization sequence

  • Dominik Urselmann,
  • Dragutin Antovic and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 1499–1503, doi:10.3762/bjoc.7.174

Graphical Abstract
  • efficiency is also variable. Just recently we reported a very straightforward one-pot synthesis of symmetric 1,4-di(hetero)arylated 1,3-butadiynes starting from (hetero)aryl iodides by virtue of a sequentially Pd/Cu-catalyzed [14] Sonogashira–Glaser process (Scheme 1) [15]. According to this general one-pot
  • structure is supported by mass spectrometry and combustion analysis. The scope of this new one-pot pseudo five-component Sonogashira–Glaser cyclization synthesis of symmetrical 2,5-di(hetero)arylthiophenes 2 is fairly broad with respect to the applied (hetero)aryl iodides 1. The product analysis of the
  • cleavage of the protection group and the formation of several byproducts were observed leading to a significantly lower isolated yield of the corresponding thiophene 2p. Conclusion In summary we have developed an economical and efficient one-pot sequence for transforming (hetero)aryl iodides into
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Published 04 Nov 2011

Amines as key building blocks in Pd-assisted multicomponent processes

  • Didier Bouyssi,
  • Nuno Monteiro and
  • Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

Graphical Abstract
  • (after removal of excess acrylic acid) with the aid of an oligomeric alkyl carbodiimide 44 (Scheme 19) [19]. Interestingly, Willis and coworkers have shown that aryl N-aminosulfonamides may be accessed by three-component coupling of aryl iodides, hydrazines, and DABCO·(SO2)2 as a convenient source of
  • and coworkers [35]. In this case, N,N-dimethyl-2-iodoanilines, terminal alkynes and various aryl iodides were involved in the reaction due to the high nucleophilicity of the N,N-dialkylamino moiety. Here, the reaction needs to be performed in two steps, the aryl iodide in acetonitrile being added
  • . Synthesis of pyrroles by cyclization of propargyl amines. Isoindolone and phthalazone synthesis by cyclization of acylhydrazides. Sultam synthesis by cyclization of sulfonamides. Synthesis of sulfonamides by aminosulfonylation of aryl iodides. Pyrrolidine synthesis by carbopalladation of allylamines
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Published 10 Oct 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
  • direct insertion of zinc dust to alkyl iodides proceeds readily, the insertion to aryl iodides is very slow in THF and requires the use of polar solvents [4] or highly activated zinc [5]. Recently, we found that the presence of LiCl greatly facilitates the insertion of zinc to aryl iodides [6]. Thus, the
  • limitation due to the use of zinc as a reducing agent. Zinc has only moderate reducing properties, therefore its insertion into organic halides only proceeds smoothly in the case of aryl iodides and electron-poor substituted aryl bromides. The use of highly reactive zinc (Rieke-zinc) [20][21] solves the
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Published 13 Sep 2011

Combined directed ortho-zincation and palladium-catalyzed strategies: Synthesis of 4,n-dimethoxy-substituted benzo[b]furans

  • Verónica Guilarte,
  • M. Pilar Castroviejo,
  • Estela Álvarez and
  • Roberto Sanz

Beilstein J. Org. Chem. 2011, 7, 1255–1260, doi:10.3762/bjoc.7.146

Graphical Abstract
  • heterocyclization. In recent years, the direct hydroxylation of aryl halides has been developed by several groups by using palladium- or copper-catalyzed protocols. Whereas the reactions under copper catalysis work well for aryl iodides [45][46][47][48], the palladium-catalyzed hydroxylation also takes place with
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Published 12 Sep 2011

Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene

  • Alexandre Pradal,
  • Chung-Meng Chao,
  • Patrick Y. Toullec and
  • Véronique Michelet

Beilstein J. Org. Chem. 2011, 7, 1021–1029, doi:10.3762/bjoc.7.116

Graphical Abstract
  • presence of diversely functionalized aryl iodides (Scheme 2). The corresponding substituted alkynes 2b–e [46] were isolated in 71–85% yield. An analogous 1,6-enyne 6 [64] was also reacted with 3-bromoiodobenzene under the same reaction conditions and led to the formation of substrate 2f in 58% isolated
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Published 26 Jul 2011
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