Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties

• Shaojin Gu,
• Jiehao Du,
• Jingjing Huang,
• Huan Xia,
• Ling Yang,
• Weilin Xu and
• Chunxin Lu

Beilstein J. Org. Chem. 2016, 12, 863–873, doi:10.3762/bjoc.12.85

• via reacting methyl propiolate with (azidomethyl)benzene. This promising catalytic behavior of complex 4 prompted us to extend our studies toward a one-pot synthesis of 1,2,3-triazoles from alkyl halides, sodium azide, and alkynes. The three-component version has already been successfully performed

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• design was used to optimize the structure to make the chloride’s affinity equal to that of bifluoride. Part (a) adapted with permission from [30], copyright 2011 Wiley. Part (c) adapted with permission from [32], copyright 2014 American Chemical Society. (a) One-pot synthesis of cyanostars. (b) Volcano

Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

• Rajeev S. Menon,
• Akkattu T. Biju and
• Vijay Nair

Beilstein J. Org. Chem. 2016, 12, 444–461, doi:10.3762/bjoc.12.47

• . This is followed by a redox esterification of the latter (47) with enals. The overall process constitutes a one-pot synthesis of hydroxamic esters 48 [45]. Notably, both steps can be performed using the single NHC catalyst 22 under same reaction conditions (Scheme 29). This two-step, one-pot synthesis

• reaction with enals. Aza-benzoin reaction of aldehydes and phosphinoylimines catalysed by the BAC-carbene. Nitrosoarenes as the electrophilic component in benzoin-initiated cascade reaction. One-pot synthesis of hydroxamic esters via aza-benzoin reaction. Cookson and Lane’s report of intramolecular benzoin

A quadruple cascade protocol for the one-pot synthesis of fully-substituted hexahydroisoindolinones from simple substrates

• Hong-Bo Zhang,
• Yong-Chun Luo,
• Xiu-Qin Hu,
• Yong-Min Liang and
• Peng-Fei Xu

Beilstein J. Org. Chem. 2016, 12, 253–259, doi:10.3762/bjoc.12.27

• one-pot cascade quadruple protocol features readily available starting materials, simple manipulation, mild conditions and good atom economy. Keywords: bifunctional catalysis; hexahydroisoindolinones; one-pot synthesis; quadruple cascade; Introduction Isoindolines and their congeners are one kind of

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• bistriazoles. The pyrene-appended thiacalix[4]arene-based bistriazole. The synthesis of triazole-based tetradentate ligands. The synthesis of phenanthroline-2,9-bistriazoles. The three-component reaction for the synthesis of bistriazoles. The one-pot synthesis of bistriazoles. The synthesis of polymer-bearing

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

• Morgan Hans,
• Jan Lorkowski,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

• tetrafluoroborate The one-pot synthesis of 1,3-dicyclohexylimidazolium chloride (ICy·HCl) was first disclosed in the open literature by Herrmann and co-workers in 1996 [47]. The reaction proceeded smoothly and the product did not show any tendency to form an ionic liquid, unlike its lower weight unsymmetrical

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

• Jing Lin,
• Tao Kong,
• Lin Ye,
• Ai-ying Zhang and
• Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

• and pentablock copolymer. The gel was washed three times with distilled water and freeze dried to get the PPRs powder products. One-pot preparation of PRs A protocol for the one-pot synthesis of PRs by endcapping PPRs via the second in situ ATRP of MPC was as follows. In a sealable Pyrex reactor, the

Recent advances in copper-catalyzed C–H bond amidation

• Jie-Ping Wan and
• Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

• of o-halobenzamides 82 and (benzo)imidazoles 87 for the one-pot synthesis of (benzo)imidazoquinazolinones 88 under the catalysis of CuI and assistance of L-proline. A subsequent oxidation using molecular oxygen was required for the final formation of products. According to the results, the mechanism

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

• Mingxing Liu,
• Jiarong Li,
• Hongxin Chai,
• Kai Zhang,
• Deli Yang,
• Qi Zhang and
• Daxin Shi

Beilstein J. Org. Chem. 2015, 11, 2125–2131, doi:10.3762/bjoc.11.229

• Mingxing Liu Jiarong Li Hongxin Chai Kai Zhang Deli Yang Qi Zhang Daxin Shi School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing, 100081, China 10.3762/bjoc.11.229 Abstract An efficient one-pot synthesis of pyrazolo[3,4-d]pyrimidine derivatives by the four

• fashion [43][44][45][46][47]. During the course of previous studies, we envisioned that we could combine these reactions and embarked on designing a strategy toward a one-pot synthesis by combining the three reactants. When benzaldehyde was used as the reactant, the target product was obtained (Scheme 1A

• the detailed mechanism and synthetic application of this protocol are in progress. Four-component one-pot synthesis of 5. Reactions conditions: 1 (1.2 mmol), 2 (1.0 mmol), 3 (1.2 mmol) and 4 (1.2 mmol) in alcohol (15 mL). Molecular structure (from X-ray diffraction data) of 5g. The synthesis of

Olefin metathesis in air

• Lorenzo Piola,
• Fady Nahra and
• Steven P. Nolan

Beilstein J. Org. Chem. 2015, 11, 2038–2056, doi:10.3762/bjoc.11.221

• ruthenium carbene. Synthesis of Grubbs' 1st generation catalyst. Access to 21 from the Grubbs’ 1st generation catalyst and its one-pot synthesis. Synthesis of supported Hoveyda-type catalyst. Synthesis of 33 by Hoveyda and Blechert. Synthesis of 41. Synthesis of Grubbs' 3rd generation catalyst. Synthesis of

Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

• Iris Binyamin,
• Shoval Meidan-Shani and
• Nissan Ashkenazi

Beilstein J. Org. Chem. 2015, 11, 1332–1339, doi:10.3762/bjoc.11.143

• elevated temperatures [44][45]. Our hypothesis was that another possible attractive route to obtain phosphine oxides would be the reaction of aryl/alkyl-oxaphospholanes with Grignard reagents. Oxaphospholane 5 was obtained according to Garner’s procedure [43] using a one pot synthesis from two commercial

One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

• Mohammad Abbasi and
• Reza Khalifeh

Beilstein J. Org. Chem. 2015, 11, 1265–1273, doi:10.3762/bjoc.11.141

• Mohammad Abbasi Reza Khalifeh Chemistry Department, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran Department of Chemistry, Shiraz University of Technology, Shiraz, Iran 10.3762/bjoc.11.141 Abstract An efficient and odourless procedure for a one-pot synthesis of thioesters by

• the thioester product cannot be produced through generation of the thioacid from thiourea and benzoyl chloride. To establish a protocol for the one-pot synthesis of thioacid derivatives via in situ generation of thioacids, considerable preliminary tests were accomplished using thiourea and carboxylic

• ; found: C, 69.80; H, 6.88; S, 15.61. One-pot procedure for the preparation of thioesters. Reaction of benzoyl chloride, thiourea and butyl acrylate. A proposed reaction pathway. One-pot synthesis of thioesters using benzoic anhydrides, thiourea and electron-deficient alkenesa. One-pot synthesis of

A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles

• Roman A. Irgashev,
• Arseny A. Karmatsky,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2015, 11, 1000–1007, doi:10.3762/bjoc.11.112

• means of the Paal–Knorr reaction. Compound 9a has also been treated with the Lawesson's reagent in toluene to give the title product 12a via intermediacy of 10a in a low 10% yield, based on the starting isatin 7a (Path A). Also the one-pot synthesis (Path D) of compound 12a has been realized through

• , 1080, 1128, 1164, 1187, 1224, 1285, 1324, 1348, 1391, 1414, 1464, 1485, 1502, 1584, 1608, 1629, 1653, 1709, 1780, 2648, 2837, 2939, 3021, 3402 cm−1; anal. calcd for C18H14N2O4: C, 67.07; H, 4.38; N, 8.69; found: C, 67.03; H, 4.12; N, 8.62. Procedure for the one-pot synthesis of thieno[2,3-b]indole 12a

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

• Hongnan Sun,
• Binbin Huang,
• Run Lin,
• Chao Yang and
• Wujiong Xia

Beilstein J. Org. Chem. 2015, 11, 524–529, doi:10.3762/bjoc.11.59

• . Furthermore, a range of optically pure morpholines could be achieved by the use of chiral aziridines. Experimental General procedure for the one-pot synthesis of morpholines: A 10 mL round bottom flask equipped with a magnetic stirring bar was charged with aziridine/azetidine 1 (0.3 mmol, 1 equiv), (NH4)2S2O8

• residue was purified by column chromatography on silica gel using ethyl acetate/hexane mixtures to afford the pure products. Pharmaceutically active 2- and 2,3-disubstituted morpholines. One-pot synthesis of morpholines through ring opening of aziridines with haloalcohols. Metal-free one-pot synthesis of

• morpholine 3a from aziridine 1a. Metal-free one-pot synthesis of optically pure morpholine derivatives from chiral aziridines. Proposed mechanism. Metal-free ring opening of 2-phenyl-N-tosylaziridine (1a) with 2-chloroethanol using different persulfates as oxidant.a Metal-free one-pot synthesis of

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• ·Et2O gave genistein (60) in good yield. In the Friedel–Crafts acylation, BF3·Et2O was used as the catalyst and solvent. The following formation of the pyrone was also catalyzed by BF3·Et2O, and a convenient one-pot synthesis of 60 was achieved without isolation of 59 [85]. Fisetin and quercetin The

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

Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

• Bianca Rossi,
• Nadia Pastori,
• Simona Prosperini and
• Carlo Punta

Beilstein J. Org. Chem. 2015, 11, 66–73, doi:10.3762/bjoc.11.10

• procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the

• : aminoalcohols; free-radical addition; imine; multicomponent reaction; titanium salts; Introduction Multicomponent reactions (MCRs) represent a green approach towards the synthesis of polyfunctionalized molecules by promoting multiple bond-forming mechanisms in a one-pot synthesis [1][2][3][4][5][6][7

• approach. In fact, our procedure requires neither the preformation of imines nor anhydrous media, due to the coordinating effect of titanium salts, which promote the one-pot synthesis of amino derivatives according to a classical MCR. The basic approach consists of the simple mixing of an aniline, an

Sequential decarboxylative azide–alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

• Kuppusamy Bharathimohan,
• Thanasekaran Ponpandian,
• A. Jafar Ahamed and
• Nattamai Bhuvanesh

Beilstein J. Org. Chem. 2014, 10, 3031–3037, doi:10.3762/bjoc.10.321

• methodology is more convenient to produce the complex polycyclic molecules in a simple way. Keywords: copper(II) acetate; decarboxylative CuAAC; dehydrogenative coupling; fused triazoles; one-pot synthesis; Introduction The copper-catalyzed Huisgen [3 + 2] cycloaddition (or copper-catalyzed azide–alkyne

• were developed for the synthesis of fused triazoles [40]. Ackermann referred to an intramolecular dehydrogenative coupling of 1,4-disubstituted triazoles to achieve tri- and tetracyclic triazoles [34]. Recently, Lautens et al. [41] described a one-pot synthesis of fused triazoles through CuAAC reaction

A one-pot multistep cyclization yielding thiadiazoloimidazole derivatives

• Debabrata Samanta,
• Anup Rana,
• Jan W. Bats and
• Michael Schmittel

Beilstein J. Org. Chem. 2014, 10, 2989–2996, doi:10.3762/bjoc.10.317

• ]. Benzimidazole-fused thiadiazoles offer the option to accommodate various substitution patterns that could act as reactivity tuners [9] and recognition sites [10] to enrich the biological scope. Herein, we report on a convenient one-pot synthesis to prepare such 1,2,4-thiadiazoles (with two identical

Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes

• Yibiao Li,
• Liang Cheng,
• Xiaohang Liu,
• Bin Li and
• Ning Sun

Beilstein J. Org. Chem. 2014, 10, 2886–2891, doi:10.3762/bjoc.10.305

• nucleophilic annulation process (Scheme 1b) [24]. But this method involves a two-step process and the usage of two different metal salts may complicate further processing. The direct design of a Pd or Cu-catalyzed one-pot synthesis of benzo[b]thiophenes from 2-bromoalkynylbenzenes and a thiol derivative has

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• and potential of this methodology are under way in our laboratory. Structures of compounds 1–3. Structure of compound 6 determined by single crystal X-ray diffractometry. Hypothetical one-pot synthesis of compound 4a and/or 4b. Evaluation of the substrate scope using RB as oxygen (1O2) sensitizer “on

A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

• Chunpu Li,
• Lei Zhang,
• Shuangjie Shu and
• Hong Liu

Beilstein J. Org. Chem. 2014, 10, 2441–2447, doi:10.3762/bjoc.10.254

Synthesis of 2-trifluoromethylpyrazolo[5,1-a]isoquinolines via silver triflate-catalyzed or electrophile-mediated one-pot tandem reaction

• Xiaoli Zhou,
• Meiling Liu,
• Puying Luo,
• Yingjun Lai,
• Tangtao Yang and
• Qiuping Ding

Beilstein J. Org. Chem. 2014, 10, 2286–2292, doi:10.3762/bjoc.10.238

• cores [11][14] and the synthesis of novel fluorinated heterocycles [27] with potential biological applications, herein, we describe an efficient method for the one-pot synthesis of trifluoromethylated pyrazolo[5,1-a]isoquinoline derivates via a Lewis acid (AgOTf) or an electrophile- (I2 or ICl) promoted

Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

• Alejandro Gimenez Molina,
• Amit M. Jabgunde,
• Pasi Virta and
• Harri Lönnberg

Beilstein J. Org. Chem. 2014, 10, 2279–2285, doi:10.3762/bjoc.10.237

• '-GMP dime by an essentially one-pot synthesis followed by a two-step, one-flask deprotection [24]. Results and Discussion Preparation of nucleosidic building blocks The synthesis of the nucleosidic building blocks is outlined in Scheme 1. The base moiety protected 2'-O-(2-cyanoethyl)-3',5'-O-(1,1,3,3

(CF₃CO)₂O/CF₃SO₃H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones

• JungKeun Kim,
• Elvira Shokova,
• Victor Tafeenko and
• Vladimir Kovalev

Beilstein J. Org. Chem. 2014, 10, 2270–2278, doi:10.3762/bjoc.10.236

• ), 28.4 (CH2), 27.5 (CH2); Anal. calcd for C18H16N2: C, 83.05; H, 6.19; N, 10.76; found: C, 82.67; H, 6.35; N, 10.37. The molecular structure of 4a. One-pot synthesis of diketone 3h from acids 1d and 1c. Scope and limitations. One-pot synthesis of pyrazoles 6. TFAA/TfOH-mediated self-acylation of ω