Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• double cyclisation reaction that requires 2 equiv of base for each tetrahydrofuran formed. The reaction mechanism is quite complex (Scheme 2) since it encompasses two carboxymethylation reactions (via BAc2) followed by two intramolecular cyclisations (via BAl2). In order to avoid the use of excess base

• applications, but also by its high reactivity and peculiar molecular structure [89]. Isosorbide has an open-book V-shaped configuration formed by two cis-connected tetrahydrofuran rings with an opening angle of 120°. The four oxygen atoms incorporated in the structure are in β-position to each other [61][62

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• -(hydroxymethyl)anthracene, respectively (Figure 1). HCP-91 and HCP-94 have been synthesized by using a Friedel–Crafts alkylation reaction. The thus obtained as-synthesized compounds were washed repeatedly with dimethylformamide (DMF), methanol, water, chloroform, dichloromethane and tetrahydrofuran (THF) to

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• using Zn(OAc)2 to a 2-step, one pot reaction with sodium hydride in tetrahydrofuran, followed by the addition of zinc(II) chloride. Zinc(II) and BF2+ chelates were purified by silica gel column chromatography to isolate the chelates as blue solids and the identity and purity was confirmed by NMR

• solvents were used as received unless otherwise specified. Xylenes and tetrahydrofuran were distilled over sodium and benzophenone, degassed and stored under nitrogen. ADP, ADPI2, WS3, BF2(WS3), and Zn(WS3)2 were synthesized and purified according to literature procedures with minor modifications [2][5][9

• reflux condenser, L1 (100 mg, 0.146 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) under N2. To this dark blue solution, anhydrous NaH (4.00 mg, 0.161 mmol) was added and the mixture was heated to 60 °C. The solution turned to bright blue. After 24 h of heating, anhydrous ZnCl2 (11.5 mg, 0.084

Experimental and theoretical investigations on the high-electron donor character of pyrido-annelated N-heterocyclic carbenes

• Michael Nonnenmacher,
• Dominik M. Buck and
• Doris Kunz

Beilstein J. Org. Chem. 2016, 12, 1884–1896, doi:10.3762/bjoc.12.178

• mL of tetrahydrofuran was cooled to −35 °C and a solution of potassium tert-butoxide (14.9 mg, 133 μmol) in 1 mL tetraydrofuran was added. After 30 min the deep red suspension was warmed up to room temperature and stirred overnight. The solvent was removed in vacuo and the residue suspended in 7 mL

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

• Mei-Yuan Hsu,
• Yi-Pei Liu,
• Sarah Lam,
• Su-Ching Lin and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

• , dimethylformamide (DMF) (64%, Table 2, entry 2) [76], acetonitrile (ACN) [74] (44%, Table 2, entry 3), tetrahydrofuran (THF) (56%, Table 2, entry 4), and dioxane [75] (50%, Table 2, entry 5) were tested as glycosylation modulators and similar yields of 25 were obtained, but their α-selectivities dramatically

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe

• Motoyuki Isoda,
• Kazuyuki Sato,
• Yurika Kunugi,
• Satsuki Tokonishi,
• Atsushi Tarui,
• Masaaki Omote,
• Hideki Minami and
• Akira Ando

Beilstein J. Org. Chem. 2016, 12, 1608–1615, doi:10.3762/bjoc.12.157

• 0.25 mm × 15 m, carrier; He). Peak areas were calculated on a Hitachi D-2500 Chromato-Integrator. Materials Tetrahydrofuran (THF) was purchased from Kanto Chemical Co. Inc. (Tokyo, Japan) in the dehydrated form. N,N-Dimethylformamide (DMF) and dichloromethane (CH2Cl2) were distilled over CaH2 and

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• mixture was stirred under reduced pressure overnight. In a glove box, copper(I) acetate (0.05 g, 0.40 mmol, 2.20 equiv) and dichloromethane or tetrahydrofuran (3 mL) were added. The suspension was stirred at room temperature for 5 d. a) Procedure for the reaction in dichloromethane: The suspension was

• reaction in tetrahydrofuran: The solvent was removed under reduced pressure and dichloromethane (4 mL) was added in the glove box. The suspension was filtered over a frit and the solution was concentrated by reducing the solvent in vacuo to 2 mL. Diethyl ether (4 mL) was added and the formed precipitate

Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

• Hee Seung Jang,
• Yubin Kim and
• Dae Young Kim

Beilstein J. Org. Chem. 2016, 12, 1551–1556, doi:10.3762/bjoc.12.149

• presence of 10 mol % of catalyst III together with ketimine 1a and diphenyl phosphonate (2). We obtained excellent results in ethyl acetate (85% yield, 90% ee, Table 1, entry 3), while a slight decrease in enationselectivities was observed when dichloromethane, chloroform, tetrahydrofuran, toluene, and

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• tetrahydrofuran formation during biosynthesis. As the enzyme must act on biosynthetic intermediates of strongly varying size, this attributes a remarkably broad substrate tolerance to PamS. No detailed characterisation of PamS has been carried out yet. Oocydin. Homologs of trans-AT-PKS-characteristic pyran

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic–organic hybrid perovskite solar cells

• Wei Li,
• Munechika Otsuka,
• Takehito Kato,
• Yang Wang,
• Takehiko Mori and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2016, 12, 1401–1409, doi:10.3762/bjoc.12.134

• GULLIVER 1500 equipped with a pump (PU-2080 Plus), an absorbance detector (RI-2031 Plus), and two Shodex GPC KF-803 columns (8.0 mm I.D. × 300 mm L) based on a conventional calibration curve using polystyrene standards. Tetrahydrofuran (40 °C) was used as a carrier solvent at the flow rate of 1.0 mL min−1

Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals

• Haipan Zhu,
• Peile Du,
• Jianjun Li,
• Ziyang Liao,
• Guohua Liu,
• Hao Li and
• Wei Wang

Beilstein J. Org. Chem. 2016, 12, 1340–1347, doi:10.3762/bjoc.12.127

• amine I in CH2Cl2 at rt for 48 h (Table 1). A series of Lewis acids were initially screened. FeCl3 and Cu(OTf)2 gave the 1,2-cycloaddition product tetrahydrofuran 4a (Table 1, entries 1 and 2). It is also disappointing that others Lewis acids, such as CuCl2, MgI2, ZnBr2, ZnCl2 and FeCl2 failed to

On the mechanism of imine elimination from Fischer tungsten carbene complexes

• Philipp Veit,
• Christoph Förster and
• Katja Heinze

Beilstein J. Org. Chem. 2016, 12, 1322–1333, doi:10.3762/bjoc.12.125

• obtained by treating W(CO)5(1Et) [20][21] with aminoferrocene (Fc-NH2) [40][41] in the presence of potassium hexamethyldisilazide (KHMDS) in tetrahydrofuran at room temperature (Scheme 2). In an analogous reactivity to Cr(CO)5(E-2) (Scheme 1a) [27], the formation of the imine E-3 is observed as a side

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp² C–H and sp³ C–H bonds

• Nivesh Kumar,
• Santanu Ghosh,
• Subhajit Bhunia and
• Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

• elaboration and functionalization. A few substrates were treated under decarboxylative allylation (DcA) conditions in the presence of 10 mol % of Pd(PPh3)4 in refluxing tetrahydrofuran (7–8 h), which afforded products 26a–d in up to 99% yield (Scheme 11). Interestingly, oxidative coupling products with

Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization

• Barry M. Trost,
• Michael C. Ryan and
• Meera Rao

Beilstein J. Org. Chem. 2016, 12, 1136–1152, doi:10.3762/bjoc.12.110

• transition metals to affect asymmetric enyne cycloisomerization [13][14][15][16][17][18][19][20][21][22][23]..In particular, Mikami has disclosed a palladium-catalyzed asymmetric enyne cycloisomerization where a tetrahydrofuran containing a quaternary, all-carbon stereocenter is created in excellent yield

Stimuli-responsive HBPS-g-PDMAEMA and its application as nanocarrier in loading hydrophobic molecules

• Yongsheng Chen,
• Li Wang,
• Haojie Yu,
• Zain-Ul-Abdin,
• Ruoli Sun,
• Guanghui Jing,
• Rongbai Tong and
• Zheng Deng

Beilstein J. Org. Chem. 2016, 12, 939–949, doi:10.3762/bjoc.12.92

• 400M spectrometer. The molecular weight of polymer was determined by gel permeation chromatography (GPC) (Waters-Wyatt) equipped with RI, UV, viscosity and LS detectors using tetrahydrofuran (THF) as eluent. The UV–vis spectra were recorded on a UV3802 (UNICO) ultraviolet spectrophotometer. The size

1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis

• Antonia Mielgo and
• Claudio Palomo

Beilstein J. Org. Chem. 2016, 12, 918–936, doi:10.3762/bjoc.12.90

• ureidopeptide-like bifunctional Brønsted base catalyst C5 [85]. Ureidopeptide-like Brønsted base bifunctional catalyst preparation. NMM = N-methylmorpholine, THF = tetrahydrofuran [85]. Selected examples of the Michael addition of thiazolones to different nitroolefins promoted by catalyst C5 [85]. Elaboration

Enantioselective carbenoid insertion into C(sp³)–H bonds

• J. V. Santiago and
• A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

• stereogenic center is formed on the carbenoid carbon coordinated to the metal rhodium center and not on carbon-containing the C(sp3)–H bond activated by the carbenoid moiety. The authors also reported in this work the insertion into the C(sp3)–H bond of tetrahydrofuran. This reaction showed good yield, regio

• in C(sp3)–H bonds in a diastereo- and enantioselective manner. For enantioselective insertion reactions the authors tested two specific iridium complexes, 61a and 61b. The authors used a wide range of α-substituted α-diazoacetates for performing insertion into substrates such as tetrahydrofuran (24

• low temperatures to affords the product in high yields and enantioselectivity (Scheme 12). The same catalytic system was applied to carbenoid insertions into tetrahydrofuran C(sp3)–H bonds (Scheme 13). The reaction afforded the desired product in a regioselective way and high diastereoselectivity

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes

• M. Emin Cinar,
• Bernward Engelen,
• Martin Panthöfer,
• Hans-Jörg Deiseroth,
• Jens Schlirf and
• Michael Schmittel

Beilstein J. Org. Chem. 2016, 12, 813–824, doi:10.3762/bjoc.12.80

• benzaldehyde (3a: Ar = Ph) (Scheme 2). The enolate was generated from propiophenone by deprotonation with lithium diisopropylamide (LDA) at −40 °C in tetrahydrofuran (THF) and was subsequently reacted with 0.33 equivalents of MCl3 or 0.25 equivalents of MCl4, respectively. The resulting metal enolate was then

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

• Qiao-Wen Jin,
• Zhuo Chai,
• You-Ming Huang,
• Gang Zou and
• Gang Zhao

Beilstein J. Org. Chem. 2016, 12, 725–731, doi:10.3762/bjoc.12.72

• influence of solvents and reaction temperature on the reaction were investigated with the best catalyst (Table 2). The use of both polar solvents (ethyl ether, tetrahydrofuran, acetone, acetonitrile or ethyl alcohol) including other chlorinated solvents such as chloroform, 1,2-dichloroethane and 1,1,2

Versatile deprotonated NHC: C,N-bridged dinuclear iridium and rhodium complexes

• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 117–124, doi:10.3762/bjoc.12.13

• functional [82]. Solvent effects, using either tetrahydrofuran, dichloromethane or toluene, were calculated with the polarizable continuous solvation model polarizable continuum model (PCM) model [83][84], and non-electrostatic terms were also included. The cavity is created via a series of overlapping

Solving the puzzling competition of the thermal C²–C⁶ vs Myers–Saito cyclization of enyne-carbodiimides

• Anup Rana,
• Mehmet Emin Cinar,
• Debabrata Samanta and
• Michael Schmittel

Beilstein J. Org. Chem. 2016, 12, 43–49, doi:10.3762/bjoc.12.6

• with the concerted C2–C6 (DA) pathway, opening new venues for the preparation of heterocycles from carbodiimides [54]. Experimental General methods. Anhydrous solvents were used to perform reactions under inert atmosphere (argon). Potassium was utilized to dry tetrahydrofuran (THF) and toluene

Iron complexes of tetramine ligands catalyse allylic hydroxyamination via a nitroso–ene mechanism

• David Porter,
• Belinda M.-L. Poon and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 2549–2556, doi:10.3762/bjoc.11.275

• commercially available reagents were used without purification unless otherwise specified. Solvents for extraction and chromatography were distilled before use. Solvents for reactions were freshly distilled immediately prior to use. Tetrahydrofuran (THF) was dried over sodium wire and benzophenone

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• by 1H NMR, 13C NMR, and EIMS. Self-assembly and SEM investigation of T1 and T2 The studies showed that T1 and T2 gels were not formed in several common solvents such as hexane, chloroform, dichloromethane, tetrahydrofuran, toluene, diethyl ether, acetone, dimethylformamide, ethanol, methanol and

Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

• Davide Bello and
• David O'Hagan

Beilstein J. Org. Chem. 2015, 11, 1902–1909, doi:10.3762/bjoc.11.205

• % yield (Table 2, entry 8). When tetrahydrofuran or dichloroethane were explored as solvents the conversions were low, even when warming (tetrahydrofuran, Table 2, entry 9, dichloroethane, Table 2, entries 10–12). For the TiF4/3HF·Et3N reactions (Table 3) shorter reaction times also afforded lower

• conversions, and sub-stoichiometric levels of TiF4 failed to initiate the reaction. Tetrahydrofuran and dichloroethane at different temperatures were again not useful solvents. Having optimised the reaction to some extent with substrate 1a, a range of alkynyl sulfides [15] were now prepared and each