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Search for "Pd(OAc)2" in Full Text gives 199 result(s) in Beilstein Journal of Organic Chemistry.

Fluorinated phenylalanines: synthesis and pharmaceutical applications

  • Laila F. Awad and
  • Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

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  • presence of Pd(OAc)2 as a catalyst. The corresponding β-fluoro derivatives 159a–v were obtained with high stereoselectivity using DCM and iPrCN as co-solvent (30:1 v/v). Interestingly reducing the Pd(OAc)2 concentration from 10 mol % to 6 mol % led to an improved yield of 73% for 159a, 159g, and 159t
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Published 15 May 2020

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes

  • Aya Yoshimura,
  • Hitoshi Kimura,
  • Kohei Kagawa,
  • Mayuka Yoshioka,
  • Toshiki Itou,
  • Dhananjayan Vasu,
  • Takashi Shirahata,
  • Hideki Yorimitsu and
  • Yohji Misaki

Beilstein J. Org. Chem. 2020, 16, 974–981, doi:10.3762/bjoc.16.86

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  • Abstract Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C–H arylation. In the presence of a catalytic amount of Pd(OAc)2, P(t-Bu3)·HBF4, and an excess of Cs2CO3, the C–H arylation of TTF with several aryl bromides
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Published 12 May 2020

Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

  • Liliia Moshniaha,
  • Marika Żyła-Karwowska,
  • Joanna Cybińska,
  • Piotr J. Chmielewski,
  • Ludovic Favereau and
  • Marcin Stępień

Beilstein J. Org. Chem. 2020, 16, 895–903, doi:10.3762/bjoc.16.81

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  • that the coupling and α-oxygenation can also be achieved with 1 equiv of Pd(OAc)2 in the presence of 2 equiv of silver carbonate. Nevertheless, Ag2CO3 oxidation provided lower yields and the efficiency of this variant was dramatically diminished when the loading of palladium(II) acetate was decreased
  • in toluene, dichloromethane and acetonitrile. The previously reported family of the boomerang bipyrroles obtained by Pd-induced double C–H bond activation [32]. Synthesis and structures of α-free and α-oxygenated bipyrrole boomerangs. Reagents and conditions: (a) 30 mM in AcOH, 3 equiv Pd(OAc)2, 6
  • equiv KOAc, 120 °C, 1 h; (b) 3 mM in AcOH, 3 equiv Pd(OAc)2, 120 °C, 1 h. Isolated yields are given for each set of conditions. M enantiomers are depicted for cNDA3O, cNMI3O, cNMI3H. n.d. = not determined. Screening of reaction conditions.a Experimental and calculateda properties of fused bipyrroles
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Published 04 May 2020

Rhodium-catalyzed reductive carbonylation of aryl iodides to arylaldehydes with syngas

  • Zhenghui Liu,
  • Peng Wang,
  • Zhenzhong Yan,
  • Suqing Chen,
  • Dongkun Yu,
  • Xinhui Zhao and
  • Tiancheng Mu

Beilstein J. Org. Chem. 2020, 16, 645–656, doi:10.3762/bjoc.16.61

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  • halogens to arylaldehydes have been developed. The homogeneous systems included Pd(OAc)2 with propyl di-tert-butylphosphinite ligand [30], Pd(acac)2 with dppm ligand [31], Pd(OAc)2 with CataCXium A ligand [32], and all of the three systems employed TMEDA as the base and toluene as the solvent. The
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Published 08 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

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  • 100 °C for one day, cooled, and filtered. The material Pd–Cu@rGO (78), as heterogeneous nanocatalyst, was prepared by anchoring Pd(OAc)2 on Cu@rGO in toluene via pyrolysis. The catalyst was highly active in one-pot condensations of alkyl/aryl-substituted triazole heterocycles with cycloadditions and
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Published 01 Apr 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

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  • oxidants [151][152][153]. To overcome these drawbacks, recently, Cho’s group synthesized carbazole derivatives using a dual photoredox-catalyzed intramolecular C−H bond amination of N-substituted 2-amidobiaryls with photoredox catalyst 14 in presence of Pd(OAc)2 as a cocatalyst under aerobic conditions
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Published 26 Feb 2020

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

  • Abhijit Paul,
  • Debnath Chatterjee,
  • Srirupa Banerjee and
  • Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

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  • -withdrawing groups, using Pd(OAc)2 as catalyst and Cu(OAc)2 as oxidant [25]. Since then, several variants of the reaction involving Pd catalysis and various oxidants have been reported for the synthesis of 3-alkenylindoles. For example, Chen et al. and Huang et al. independently reported the C3 alkenylation
  • of indoles using Pd(OAc)2 and Pd(II)/polyoxometallate, respectively, as a catalyst and molecular oxygen as the oxidant [26][27]. Verma and co-workers used the reaction between indoles and alkenes in the presence of a Pd(OAc)2 catalyst, a Cu(OAc)2 oxidant, and a 2-(1-benzotriazolyl)pyridine ligand [28
  • ]. Noël and co-workers reported the C3–H olefination of indoles using Pd(OAc)2 as a catalyst and molecular oxygen as the oxidant under continuous flow conditions [29]. Jia et al. reported the synthesis of 3-alkenylindoles using Pd(OAc)2 as the catalyst and MnO2 as the oxidant under ball milling conditions
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Published 29 Jan 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

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  • with a 1.61 M solution of P(t-Bu)3 (395 µL, 636 µmol, 15 mol %) in dry toluene. All following operations were carried out in a fume hood under Schlenk conditions. tert-Butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate (1.00 g, 4.25 mmol, 1.00 equiv), 15 (1.82 g, 4.24 mmol, 1.00 equiv), Pd(OAc)2 (144 mg
  • carried out in a fume hood under Schlenk conditions. Compound 15 (1.80 g, 4.19 mmol, 1.00 equiv), tert-butyl 1-(4-methoxyphenyl)hydrazine-1-carboxylate (1.04 g, 4.36 mmol, 1.04 equiv), Pd(OAc)2 (145 mg, 633 µmol, 15.1 mol %), and Cs2CO3 (2.07 g, 6.29 mmol, 1.5 equiv) were added and suspended in dry
  • conditions. To the Schlenk tube, 16a (100 mg, 172 µmol, 1.00 equiv), N-Boc-N-phenylhydrazine (110 mg, 528 µmol, 3.08 equiv), Pd(OAc)2 (2 mg, 9 µmol, 5 mol %), and Cs2CO3 (170 mg, 522 µmol, 3.04 equiv) were added. After the addition of dry toluene (1.7 mL), the mixture was stirred at rt for 30 min. Then, the
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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

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  • compounds 1 and 2, was successfully achieved. We used tri(o-tolyl)phosphine (P(o-tol)3, palladium(II) acetate (Pd(OAc)2) and obtained the desired product (E)-benzyl 3-(6-aminopyridin-3-yl)acrylate in 86% yield (see Supporting Informaiton File 1). However, when the same conditions were applied to alkyl 3-(6
  • the reaction temperature to 110 °C and prolonged the time to 50 min (Table 1, entry 3) and obtained product 3 with 58% yield. Then, we reduced the loading of the ligand, P(o-tol)3 and catalyst Pd(OAc)2, to one fourth of the loading used in the previous experiment which improved the yield of the
  • ), or even complete lack of conversion as in the case of tricyclohexylphosphine (P(Cy)3 (Table 1, entries 8–10). Also no reaction was observed in the absence of Pd(OAc)2 and P(o-tol)3, while partial conversion into product 3 occurred in the presence of Pd(OAc)2 (Table 1, entries 11 and 12). In addition
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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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  • that while Pd(PPh3)4, palladium acetate (Pd(OAc)2), PdCl2(PPh3)2, and tris(dibenzylideneacetone)dipalladium (Pd2(DBA)3) all catalyzed the Sonogashira reaction, the PdCl2(PPh3)2 precursor turned out to have the best activity in the light of reaction rates (Figure 1). In the presence of 0.5 mol % of
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Published 03 Dec 2019

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

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  • ). As compared to Pd2(dba)3, the use of Pd(OAc)2 as the Pd source resulted in a decrease of the yield (52%). Performing the reaction in dioxane or DMF gave lower yields as well. In summary, up to 75% yield of 5b could be achieved using BINAP and Pd2(dba)3 as the catalytic system. Subsequently, the scope
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Published 22 Nov 2019

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

  • Lei Zhang,
  • Greta Linden and
  • Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

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  • )aminoethyl]glycine residue –Aeg(Alloc)– was selectively deprotected in the presence of Pd(OAc)2, Ph3P, NMM, PhSiH3 in CH2Cl2 for 2 h. Subsequently, carboxy photoswitches were introduced using Oxyma and N,N’-diisopropylcarbodiimide (DIC) as coupling agent. We explored two different types of photoswitches
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Published 22 Oct 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

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Published 23 Sep 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

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  • ) appropriate boronic acid, Pd(PPh3)4, Na2CO3, DMF, H2O, microwave, 15 min, 150 °C, 43–64%. Reagents and conditions: a) Pd2(dba)3 or Pd(OAc)2, P(o-tol)3, TEA, DMF, 120–140 °C, 0.7–24 h, 11–75%; b) potassium vinyltrifluoroborate, Cs2CO3, PdCl2(PPh3)2, ACN, H2O, 1.5 h, 120 °C, 78% c) tributylvinyltin, Pd(PPh3)4
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Published 16 Sep 2019

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

  • Hai-Yun Huang,
  • Haoran Li,
  • Thierry Roisnel,
  • Jean-François Soulé and
  • Henri Doucet

Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204

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  • heteroaromatics [38], we initially employed 1 mol % Pd(OAc)2 catalyst associated to KOAc as the base in DMA at 150 °C as the reaction conditions to promote the coupling of lilolidine with 3-bromobenzonitrile (Table 1, entry 1). Under these conditions a mixture of the α- and β-arylated lilolidines 1a and 1b was
  • obtained in a 64:36 ratio. Then, the influence of some bases on the regioselectivity with Pd(OAc)2 catalyst was examined. With CsOAc a similar regioselectivity than with KOAc was obtained, whereas the use of NaOAc afforded the products 1a and 1b in an 85:15 ratio, but with a moderate conversion of 3
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Published 29 Aug 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

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  • for efficient syntheses of IPs [20]. In recent years much attention has been paid towards the exploration of transition metals (TMs) as homogeneous as well as heterogeneous catalytic system like Pd(OAc)2 [21], CuI [22], ZnO [23], ZnI2 [24], Cu(OTf)2 [25], Sc(OTf)3 [26], RuCl3 [27], [Cp*RhCl2]2 (Cp
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Published 19 Jul 2019

Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation

  • Yang Liu,
  • Julie Oble and
  • Giovanni Poli

Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107

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  • for [3 + 2] C–C/N–C bond-forming annulation [31], the first tests were performed with the following two catalytic systems: [Pd(η3-C3H5)Cl]2 (5 mol %), dppf (15 mol %)], and [Pd(OAc)2 (10 mol %), dppb (15 mol %)] in THF at room temperature (Table 1, entries 1 and 2). These conditions promptly (ca. 1
  • hour) generated annulated product 4a arising from C-allylation (C–C bond forming)/intramolecular O-Michael addition (O–C bond forming) sequence. The purification of the crude reaction was easier using the Pd(OAc)2 and dppb system (Table 1, entry 2), which was thus chosen to continue the optimization
  • ). The above work allowed obtaining the optimal reaction conditions for the generation of the furocycloalkanone 4a [Pd(OAc)2 (10 mol %), dppb (15 mol %) in DMSO, 1 h at rt (conditions A)] as well as for the formation of the bicyclo[4.3.0]nonane-3,8-dione (5a) [Pd(OAc)2 (10 mol %), dppb (15 mol %) in DMSO
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Published 16 May 2019

Mechanochemistry of supramolecules

  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

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  • azobenzene [58]. The cyclopalladation process was proved to be a highly regioselective process and the observed palladation rate was faster compared to the conventional solution-phase method. An equimolar amount of 4'-(N,N-dimethylamino)-4-nitroazobenzene and Pd(OAc)2 in the presence of 25 μL of glacial
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Published 12 Apr 2019

A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

  • Yue Zhong,
  • Wen-Yu Wu,
  • Shao-Peng Yu,
  • Tian-Yuan Fan,
  • Hai-Tao Yu,
  • Nian-Guang Li,
  • Zhi-Hao Shi,
  • Yu-Ping Tang and
  • Jin-Ao Duan

Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26

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  • (PPh3)4/PPh3 as the catalyst, Cs2CO3 as base, and dimethyl formamide (DMF) as solvent at 105 °C for 10 h under N2 atmosphere. Meanwhile, different pallladium species were tested in this reaction system. It was found that Pd(OAc)2 was the most effective palladium catalyst, and the desired product y-1 was
  • (1a, 3.0 mmol, 1.0 equiv, 0.654 g), 2-bromo-4,5-dimethoxybenzoyl chloride (3.6 mmol, 1.2 equiv, 1.006 g), and norbornadiene (6.0 mmol, 2.0 equiv, 0.553 g) was performed in the presence of 0.15 mmol of Pd(OAc)2, 0.375 mmol of PPh3 and 6.75 mmol of Cs2CO3 at 105 °C in DMF under N2 for 30 h, the desired
  • with aryl iodide (0.30 mmol, 1.0 equiv), ortho-bromobenzoyl chlorides (0.36 mmol, 1.2 equiv), norbornadiene (0.60 mmol, 2.0 equiv), Pd(OAc)2 (5 mol %), triphenylphosphine (12.5 mol %), Cs2CO3 (0.675 mmol, 2.25 equiv), and DMF (4 mL). The mixture was stirred at 105 °C under nitrogen atmosphere for 10 h
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Published 31 Jan 2019

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

  • Pierre-Antoine Nocquet,
  • Aurélie Macé,
  • Frédéric Legros,
  • Jacques Lebreton,
  • Gilles Dujardin,
  • Sylvain Collet,
  • Arnaud Martel,
  • Bertrand Carboni and
  • François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

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  • vinyl ethers 15 [13][44][45][46]. We found that the best yields were obtained using Pd(TFA)2 and n-butyl vinyl ether as solvent in the presence of bathophenanthroline as ligand. In the case of Pd(OAc)2, the reaction was slower with moderate yields. The ring-closing metathesis reaction was performed with
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Published 29 Nov 2018

Pd-Catalyzed microwave-assisted synthesis of phosphonated 13α-estrones as potential OATP2B1, 17β-HSD1 and/or STS inhibitors

  • Rebeka Jójárt,
  • Szabolcs Pécsy,
  • György Keglevich,
  • Mihály Szécsi,
  • Réka Rigó,
  • Csilla Özvegy-Laczka,
  • Gábor Kecskeméti and
  • Erzsébet Mernyák

Beilstein J. Org. Chem. 2018, 14, 2838–2845, doi:10.3762/bjoc.14.262

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  • Pd sources, namely Pd(PPh3)4 or Pd(OAc)2 were used, the latter without the addition of any mono- or bidentate P-ligand. Although Et3N can usually be used successfully, the dealkylation of the phosphite reagent may occur. In order to avoid this unwanted side reaction, K2CO3 was also involved in
  • [29]; namely, 1 equiv in the case of Pd(PPh3)4 and 1.3 equiv when using Pd(OAc)2. It was earlier established that in the microwave-assisted Pd(II)-catalyzed C–P coupling of aryl bromides and dialkyl phosphites, an excess of the applied dialkyl phosphite may serve as phosphorus ligand and reducing
  • the yields of the C–P couplings. Reactions with catalyst precursor Pd(OAc)2 gave the desired phosphonate 8a in moderate yields (Table 1, entries 1–8). Starting from 2-iodo compound 1I, dehalogenation, an unwanted side reaction occurred, in particular, at elevated temperature (Table 1, entries 3, 4, 7
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Published 14 Nov 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

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  • derivative 134 was realized in the presence of a Pd(OAc)2 catalyst with the aid of the ligand cataCXium A (135) to generate the macrocyclic product 136. Eventually, synthesis of MK-6325 (141) was achieved by adopting saponification followed by amidation (Scheme 20). Conclusion In this review, we have
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Published 21 Sep 2018

Synthesis and characterization of π–extended “earring” subporphyrins

  • Haiyan Guan,
  • Mingbo Zhou,
  • Bangshao Yin,
  • Ling Xu and
  • Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

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  • . Experimentally, 3Pd can be formed quantitatively by simply mixing Pd(OAc)2 with a CH2Cl2/MeOH solution of 3 at room temperature. This transformation is confirmed by MS with a parent-ion peak at m/z = 1015.24 (calcd for C64H46BN6Pd, [M]+ = 1015.29). In the 1H NMR spectrum of 3Pd (Figure 3), no signals are
  • air, rt, overnight; (iii) Pd(OAc)2 (3 equiv), CH2Cl2/MeOH 5:1, rt, overnight. Supporting Information Supporting Information File 304: Experimental part. Supporting Information File 305: Crystallographic information file of compound 3. Supporting Information File 306: Crystallographic information file
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Published 30 Jul 2018

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

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  • (PPh3)4 as catalyst, no conversion was observed, whereas the reaction could be achieved with Pd(OAc)2 as a catalyst and water as a solvent (Table 1, entries 1–5). Thus, the latter reaction conditions were used for the synthesis of 9-arylbenzo[b]quinolizinium derivatives 1b–d (Scheme 1, Table 1). The
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Published 23 Jul 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

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  • , arenes and heteroarenes [43][44]. A first solution to value the 2-iodobenzoic moiety released from EBX has arisen from the reaction of derivatives 22 with N-(aryl)imines 23 in the presence of 10 mol % of Pd(OAc)2, which gives access to tri- or tetrasubstituted furans 24 and N-(aryl)formamides 25 (Scheme
  • of Pd(OAc)2 in THF, and affords the dibenzoalkylidenefluorene 47 in an excellent 88% yield (Scheme 16). Ten years later, Huang, Wen and co-workers have demonstrated that, in the presence of both a terminal alkyne and a boronic acid, various cyclic diaryl-λ3-iodanes undergo a transition-metal
  • be resubmitted to the cyclization conditions in the presence of a different terminal alkyne, or an activated alkene. The same authors have then showed that the reaction of cyclic diaryl-λ3-iodanes in the presence of internal alkynes and the catalytic system Pd(OAc)2-PCy3 affords functionalized
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Published 21 Jun 2018
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