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

• . 10 mmHg). The oily residue was purified by chromatography on silica gel (Merck Silicagel 60 (0.063−0.200 mm) for column chromatography (70−230 mesh ASTM)) eluted with n-pentane/EtOAc. The purity of the isolated products was >98%. The detailed experimental procedure as well as the characterization of

• (8).a Supporting Information Supporting Information File 558: Source of chemicals, the detailed experimental procedure as well as characterization data of isolated compounds. Acknowledgements This work was funded by the National Research, Development and Innovation Office – NKFIH (KH 129508 and

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• studied. Further studies are required to fully explore its activity profile. Moreover, their HDAC inhibitory effects remain to be evaluated. Studies will be continued along these directions [40][41][42][43][44]. Experimental Procedure for the synthesis of anilides 7a–g These were prepared following the

Mechanochemical synthesis of hyper-crosslinked polymers: influences on their pore structure and adsorption behaviour for organic vapors

• Sven Grätz,
• Sebastian Zink,
• Hanna Kraffczyk,
• Marcus Rose and
• Lars Borchardt

Beilstein J. Org. Chem. 2019, 15, 1154–1161, doi:10.3762/bjoc.15.112

• 35 minutes. After the synthesis, the resulting polymers were washed with 200 mL of water and 100 mL of ethanol and dried at 80 °C for 12 hours to yield a beige powder (denoted NG-HCP (neat grinding-HCP)). For more details on the experimental procedure see Supporting Information File 1. After

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• the positive and negative signs of the molecular orbital wave function, respectively. Experimental procedure for cell studies The Human breast adenocarcinoma cell line MCF-7, and normal mammary epithelial cell line MCF10A were ordered from Food Industry Research and Development Institute (Taiwan). MCF

Gold-catalyzed ethylene cyclopropanation

• Silvia G. Rull,
• Andrea Olmos and
• Pedro J. Pérez

Beilstein J. Org. Chem. 2019, 15, 67–71, doi:10.3762/bjoc.15.7

• experiments, we tested several group 11 metal-based catalysts that have been described in our group for the catalytic transfer of the CHCO2Et group from ethyl diazoacetate (N2=CHCO2Et, EDA), as well as a rhodium-based catalyst. The experimental procedure started upon placing the catalyst (0.02 mmol) into a

Synthesis of indole–cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process

• Muthumani Muthu,
• Rakkappan Vishnu Priya,
• Abdulrahman I. Almansour,
• Raju Suresh Kumar and
• Raju Ranjith Kumar

Beilstein J. Org. Chem. 2018, 14, 2907–2915, doi:10.3762/bjoc.14.269

• –cyclododeca[b]pyridine-3-carbonitrile 7f. Yields and melting points of 7 and 14. Synthesis of indole–cyclododeca[b]pyridine-3-carbonitriles 12. Yields and melting points of 15–18. Supporting Information Supporting Information File 276: Experimental procedure, compound characterization data and copies of NMR

Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

• Toshifumi Dohi,
• Shohei Ueda,
• Kosuke Iwasaki,
• Yusuke Tsunoda,
• Koji Morimoto and
• Yasuyuki Kita

Beilstein J. Org. Chem. 2018, 14, 1087–1094, doi:10.3762/bjoc.14.94

• . Experimental Representative experimental procedure for the benzylic C–H acetoxylation by the PIDA/NaBr system In a flame-dried two-necked round-bottomed flask, under nitrogen, phenyliodine(III) diacetate (PIDA, 193 mg, 0.6 mmol) and finely powdered sodium bromide (103 mg, 1.0 mmol) were subsequently added to a

• , 22.1, 56.3, 71.3, 110.3, 111.2, 113.3, 127.6, 128.7, 135.8, 156.0, 170.2 ppm; IR (KBr): 2984, 2158, 1741, 1603, 1499, 1370, 1291, 1242, 1208, 1062, 1023 cm−1; HRMS (MALDI): [M + Na]+ calcd for C12H13NO3SNa, 274.0507; found, 274.0508. Representative experimental procedure for the benzylic C–H

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

• Takayuki Yakura,
• Tomoya Fujiwara,
• Akihiro Yamada and
• Hisanori Nambu

Beilstein J. Org. Chem. 2018, 14, 971–978, doi:10.3762/bjoc.14.82

• for oxidation of alcohol, especially benzylic alcohols. Experimental Typical experimental procedure for the oxidation of secondary alcohols 14a–f: Secondary alcohol 14 (0.50 mmol) was added to a solution of the catalyst (0.15 mmol) and Bu4NHSO4 (170 mg, 0.50 mmol) in a mixture of MeNO2 (1.6 mL) and

• NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give pure ketone 15 and the catalyst. Typical experimental procedure for the oxidation of primary alcohols 14g–k: Primary alcohol 14 (0.50 mmol) was added to a

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• conjugation with the therapeutic payload. The overall experimental procedure to synthesize a PDC is usually rapid and facile. Notably, the overall cost to produce a PDC, where an already approved drug can be selected and re-used from a pool of available cytotoxic agents, is much lower compared to the cost of

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

• Mattias Bood,
• Sangamesh Sarangamath,
• Moa S. Wranne,
• Morten Grøtli and
• L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

• , however, it lacked a full experimental procedure (Scheme 7). The synthesis started from 6-chloro-7-iodo-7-deazapurine functionalized at the N-9 position with Hoffer’s α-chloro sugar (31, Scheme 7). This material was functionalized further using a Stille coupling to afford a mono-Boc-protected o

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

• Yaochun Xu,
• Isabelle Correia,
• Tap Ha-Duong,
• Nadjib Kihal,
• Jean-Louis Soulier,
• Julia Kaffy,
• Benoît Crousse,
• Olivier Lequin and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

• compounds. Additional NMR data, computational methods and additional figures and tables. Experimental procedure for fluorescence-detected ThT binding assay and representative curves of ThT fluorescence assays. Acknowledgements Central Glass Co. Ltd. is gratefully acknowledged for kindly providing fluoral

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides

• Irwan Iskandar Roslan,
• Kian-Hong Ng,
• Gaik-Khuan Chuah and
• Stephan Jaenicke

Beilstein J. Org. Chem. 2017, 13, 2739–2750, doi:10.3762/bjoc.13.270

• parameters for the synthesis of benzo[d]imidazo[2,1-b]thiazoles 3a.a Optimization parameters for the synthesis of benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ones 5a.a Supporting Information Supporting Information File 398: Experimental procedure, analytical data and NMR spectra. Acknowledgements Financial

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides

• Valentin A. Rassadin,
• Mirko Scholz,
• Anastasiia A. Klochkova,
• Armin de Meijere and
• Victor V. Sokolov

Beilstein J. Org. Chem. 2017, 13, 1932–1939, doi:10.3762/bjoc.13.187

• ; b) Pd(OAc)2, Ph3P, NaH, dioxane, 90 °C, 20 h. An attempted and a successful removal of the PMB group from the sultam 10a. Optimization of the reaction conditions for the Pd-catalyzed cyclization of the sulfonamide 8a. Supporting Information Supporting Information File 144: Experimental procedure

NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones

• Ken Takaki,
• Makoto Hino,
• Akira Ohno,
• Kimihiro Komeyama,
• Hiroto Yoshida and
• Hiroshi Fukuoka

Beilstein J. Org. Chem. 2017, 13, 1816–1822, doi:10.3762/bjoc.13.176

• 12 and its reactivity. Resting state of the monoacylated Breslow intermediate C. Reaction of benzil (1a) with ynones 2a. Reaction of substituted benzils 1 with ynone 2aa. Supporting Information Supporting Information File 274: Experimental procedure, characterization data and copies of 1H and 13C

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

• Carolina S. García,
• Paula M. Uberman and
• Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

• by transmission electron microscope (TEM) images. Representative procedure for MW-assisted Mizoroki–Heck coupling reactions The experimental procedure for MW-assisted Mizoroki–Heck coupling reactions was carried out analogously to the procedure previously reported [47]. Into a 10 mL MW tube equipped

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

• Kohei Yamada,
• Naoto Kamimura and
• Munetaka Kunishima

Beilstein J. Org. Chem. 2017, 13, 1478–1485, doi:10.3762/bjoc.13.146

• improved conditions. Screening of reaction conditions of Suzuki–Miyaura coupling with 3aa. Synthesis of various trisubstituted oxazoles. Supporting Information Supporting Information File 96: General information, Table S1, experimental procedure and characterization data for products, and 1H and 13C NMR

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

• Chandra Kant Maurya,
• Avik Mazumder and
• Pradeep Kumar Gupta

Beilstein J. Org. Chem. 2017, 13, 1184–1188, doi:10.3762/bjoc.13.117

• reducing agents, as required by the reported methods. In this way, this method presents an attractive method for the preparation of thiols which, in addition, can be useful for the generation of a thiol functional group during a total synthesis. Experimental General experimental procedure: In a three-neck

• phosphorus pentasulfide. Effect of reaction medium and reagents on conversion of thiocyanates to thiols.a Conversion of different thiocyanates to thiols with P2S5 in refluxing toluenea. Supporting Information Supporting Information File 132: Typical experimental procedure, 1H and 13C spectra of 7, 8, 11, 15

Effect of the ortho-hydroxy group of salicylaldehyde in the A³ coupling reaction: A metal-catalyst-free synthesis of propargylamine

• Sujit Ghosh,
• Kinkar Biswas,
• Suchandra Bhattacharya,
• Pranab Ghosh and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 552–557, doi:10.3762/bjoc.13.53

• intermediates. Various metal-catalyzed methods for the synthesis of propargylamine. Plausible mechanism for the metal-free A3 coupling from salicylaldehyde. Optimization of metal-catalyst-free A3 coupling reaction. Supporting Information Supporting Information File 320: Experimental procedure, characterization

Development of chiral metal amides as highly reactive catalysts for asymmetric [3 + 2] cycloadditions

• Yasuhiro Yamashita,
• Susumu Yoshimoto,
• Mark J. Dutton and
• Shū Kobayashi

Beilstein J. Org. Chem. 2016, 12, 1447–1452, doi:10.3762/bjoc.12.140

• amide catalysts in other reactions are ongoing. Experimental A general experimental procedure for conducting catalytic asymmetric [3 + 2] cycloaddition reactions with 0.01 mol % catalyst loading is described. Under an Ar atmosphere, a solution of the preformed chiral CuHMDS catalyst [prepared from KHMDS

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

• Gastón Silveira-Dorta,
• Sergio J. Álvarez-Méndez,
• Víctor S. Martín and
• José M. Padrón

Beilstein J. Org. Chem. 2016, 12, 957–962, doi:10.3762/bjoc.12.94

• Discussion The experimental procedure for the tandem reduction–Wittig olefination synthesis of allylic amines reported the use of toluene as solvent for the reduction step and THF as solvent to prepare the phosphonium ylide [17]. Consequently, the Wittig olefination takes place in a 2:1 (toluene/THF) solvent

Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

• Gergely L. Tolnai,
• Jonathan P. Brand and
• Jerome Waser

Beilstein J. Org. Chem. 2016, 12, 745–749, doi:10.3762/bjoc.12.74

• alkynylation of dipeptide 4a. Supporting Information Supporting Information File 148: Experimental procedure and characterization data for all compounds. NMR spectra of new compounds. Acknowledgements We thank the EPFL for funding and F. Hoffmann-La Roche Ltd. for an unrestricted research grant. The work of

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

• Mamoru Tobisu,
• Takuya Igarashi and
• Naoto Chatani

Beilstein J. Org. Chem. 2016, 12, 654–661, doi:10.3762/bjoc.12.65

• ) complex bearing an ICy ligand was the most efficient catalyst. The initially formed aminoborylated products can readily be converted to the corresponding organoboron compounds bearing various boron-protecting groups. Experimental Procedure for the Ir-catalyzed borylation of heteroarenes using 1g In a

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• show any fluorine incorporation. Various types of compounds resulting from the migration of the tertiary acetate to the primary position, elimination reaction or cyclization were identified depending on the experimental procedure. From these results, the fluorination was finally investigated on myo-22

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

• -methylphenyl)imidazolium chloride (IDip*·HCl or IPr*·HCl). Keywords: cyclization; experimental procedure; imidazolinium salt; imidazolium salt; microwave heating; Introduction Since Arduengo and co-workers successfully isolated and characterized the first imidazol-2-ylidene derivative in 1991 [1][2], stable

• , Figure 1). For each target compound, we strove to put together the most straightforward, detailed experimental procedure that was checked to afford high yield and purity, and a full characterization by 1H and 13C NMR spectroscopies. Results and Discussion Synthesis of 1,3-dicylohexylimidazolium

• ]. Furthermore, this last reagent does not lead to the formation of water, which can hydrolyze the starting diimine and has a deleterious influence on the reaction course. Thus, we adopted the experimental procedure carefully optimized by Hintermann to obtain IMes·HCl in ca. 85% yield (Scheme 5). We were also

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

• Svetlana F. Malysheva,
• Alexander V. Artem’ev,
• Nina K. Gusarova,
• Nataliya A. Belogorlova,
• Alexander I. Albanov,
• C. W. Liu and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2015, 11, 1985–1990, doi:10.3762/bjoc.11.214

• substrate scope for the aerobic addition of phosphine oxides 1a–f to vinyl sulfides 2a–c.a Supporting Information Supporting Information File 411: General remarks, experimental procedure and characterization data; crystallographic information for 3d; 1H, 13C & 31P NMR spectra of synthesized compounds