423 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-QZRDVUOPVS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle & Jérôme Klein
2-Azido-3-phenylquinoxaline, Potassium iodine and Sodium azide were dissolved in DMF and heated to reflux until TLC shows the end of reaction (3h). Ethyl acetate and dist water were then added. The organic layer was then washed with brine (3x). The organic layer was then dried over Na2SO4 and the solvent was then removed. The product was purified with chromatography column chromatography (1:10 EtOAc/Cyclohexane) to afford a yellowish solid.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MVJGJYRFWK-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
1H-Indole (250 mg, 2.1 mmol, 1.00 equiv) was dissolved in 10 mL of abs. methylene chloride (N2 atmosphere) and dimethylalumanylium;chloride in hexane (1 M, 2.56 mL, 2.6 mmol, 1.20 equiv) was added at 0 °C. The reaction was stirred for 15 min at 0 °C and 2-phenylacetyl chloride (330 mg, 282 μL, 2.13 mmol, 1.00 equiv) was added. The reaction was allowed to come to room temperature and was stirred at 21 °C for 14...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VOWUHKQBOI-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
1-H Indole (1.00 g, 8.54 mmol, 1.00 equiv) was dissolved under inert atmosphere in 50 mL of dry DMF. Sodium hydride (512 mg, 12.80 mmol, 1.50 equiv) and 1-bromooctane (1.98 g, 1.77 mL, 10.2 mmol, 1.20 equiv) were added at 0 °C and the reaction was stirred over night at 21 °C.The workup of the reaction was done by pouring the reaction on ice and extraction of the organic phases with ethyl acetate. The combined...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AMOBBDHYJV-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Steven Susanto
Methyl 2-(bromomethyl)prop-2-enoate (16.0 g, 89 mmol, 1.00 equiv) was dissolved in 200 mL of THF and 200 mL of dest. water. Ethanethioic S-acid (10.2 g, 9.54 mL, 134 mmol, 1.50 equiv) was added and the mixture was cooled to 0 °C. Disodium carbonate (14.2 g, 134 mmol, 1.50 equiv) was added and the resulting mixture was stirred at 21 °C for 2 h. After disappearance of the starting material (TLC control) the reaction was diluted...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-GXKYJSRHQM-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.437 M in Et2O, 437 μmol, 1.00 equiv) was added to a solution of (benzyldisulfanyl)methylbenzene (323 mg, 1.3 mmol, 3.00 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via HPLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KPGPIQKEKA-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Jérôme Klein
In a 100 mL pear-shaped flask, phosphoryl chloride (46.4 mL, 496.8 mmol, 60 eq), was added to 3-phenylquinoxalin-2(1H)-one (1840 mg, 8.3 mmol, 1 eq) and heated to 100 °C for 2 h. The reaction was cooled to 21 °C and poured on ice and rested for overnight. The remaining aqueous layer was extracted with DCM (3x) and the organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AXGWEHWIGI-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
A 1 M thiophenol solution in diethyl ether (165 mg, 1.50 mL, 1.5 mmol, 2.87 equiv) was added to the propellane solution (1.00 mL) and the mixture was stirred for 15 min at 21 °C. The solution was diluted with 10 mL of pentane and was washed with 10 mL of a 1 M NaOH solution. The organic layer was dried by the addition of Na2SO4. The mixture was filtered through a glass funnel and...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-IPOJHZYBCZ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.40 M in Et2O, 400 μmol, 2.00 equiv) was added to a solution of the 1,3-dichloro-5-[(3,5-dichlorophenyl)disulfanyl]benzene (71.2 mg, 200 μmol, 1.00 equiv) in 1.00 mL of THF under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-MRDPMFJFXN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär & Martin Nieger
The propellane solution (28.9 mg, 1.00 mL, 437 μmol, 1.00 equiv) was added to a solution of (phenyldisulfanyl)benzene (143 mg, 655 μmol, 1.50 equiv) and 1-methoxy-4-[(4-methoxyphenyl)disulfanyl]benzene (182 mg, 655 μmol, 1.50 equiv) in THF (1.00 mL) under argon atmosphere and the mixture was irradiated with UV light (500 W) for 20 min. After evaporation of the solvent under reduced pressure, the crude residue was purified via column chromatography and preparative TLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VTOQYSGXCL-UHFFFADPSC-NUHFF-NAWTY-NUHFF-ZZZ

Stefan Marschner & Thomas Wiesner
A Schlenk flask was charged with 123 mg of rac-4-stannyl-[2.2]paracyclophane (247 µmol, 2.00 equiv.), 94 mg of (5‑(4-bromophenyl)-10,15,20-triphenyl-porphyrinato)-zinc(II) (124 µmol, 1.00 equiv.), 15.3 mg of Pd(PPh3)4 (13.2 µmol, 10 mol%),, 11.2 mg of LiCl (264 µmol, 2.10 equiv.) and 38.0 mg of CuBr (264 µmol, 2.10 equiv.). Then 4 mL of dry dimethylformamide were added under argon atmosphere and the reaction mixture was degassed using three freeze-pump-thaw cycles. Then the reaction mixture was stirred at...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-QFUYDAGNUJ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
Tert-butyl nitrite (1.83 g, 2.11 mL, 18 mmol, 3.00 equiv) was added to a solution of para-toluenesulfonic acid monohydrate (3.37 g, 18 mmol, 3.00 equiv) in acetonitrile (25.0 mL), followed by 2-phenylaniline (1.00 g, 5.9 mmol, 1.00 equiv). After consumption of the starting material, potassium iodide (4.90 g, 30 mmol, 5.00 equiv), dissolved in 5 mL water, was added slowly and the mixture was stirred for 2 h at 21 °C. The product was extracted...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-IYPNRTQAOX-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Christoph Zippel
1,4-Bis(bromomethyl)benzene (10.0 g, 38 mmol, 1.00 equiv.) and thiourea (5.77 g, 76 mmol, 2.00 equiv.) were dissolved in degassed, dry ethanol (100 mL) and were stirred for 4 hours. The solvent was removed under reduced pressure to afford the crude thiouronium salt as a white solid. Sodium hydroxide (degassed 5 M aq. solution, 30 mL) was added and the reaction was heated to reflux for 30 min. The solution was cooled to 0 °C and...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-IRICWKXXVN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Christoph Zippel
Ethyl 4-aminobenzoate (1.50 g, 9.08 mmol, 1.00 equiv) was dissolved in a mixture of fluoroboric acid (48 wt% in water, 3.1 mL) and water (3.7 mL). After cooling to 0 °C, sodium nitrite (627 mg, 9.08 mmol, 1.00 equiv) in water (1.4 mL) was added. The mixture was stirred for 30 minutes.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-TVEJSJXJGY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Daniel Knoll
In a vial fitted with a magnetic stirring bar, potassium 4-trifluoroborate[2.2]paracyclophane (994.9 mg, 2.53 mmol, 1.50 equiv.), potassium phosphate (1433.0 mg, 6.75 mmol, 4.00 equiv.), palladium acetate (18.9 mg, 0.08 mmol, 0.05 equiv.), and RuPhos (118.1 mg, 0.25 mmol, 0.15 equiv.) were placed. The vial was evacuated and backfilled with argon three times. After addition of the solvent (toluene/water 10:1, 0.1 M), the respective bromide (284.0 µL, 1.69 mmol, 1.00 equiv.) was added via syringe....

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KQCLIPDQNR-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Daniel Knoll
In a vial fitted with a magnetic stirring bar, potassium 4-trifluoroborate[2.2]paracyclophane (396.8 mg, 1.26 mmol, 1.50 equiv.), potassium phosphate (714.9 mg, 3.37 mmol, 4.00 equiv.), palladium acetate (9.5 mg, 0.04 mmol, 0.05 equiv.), and RuPhos (58.9 mg, 0.13 mmol, 0.15 equiv.) were placed. The vial was evacuated and backfilled with argon three times. After addition of the solvent (toluene/water 10:1, 0.1 M), the respective bromide (104 µL, 0.84 mmol, 1 eqiv.) was added via sirringe....

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-LETIJSOCWB-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Helena Šimek
An oven-dried flask was charged with o-iodoaniline (150.0 mg, 0.68 mmol, 1.0 equiv.), 1-(bromomethyl)-4-(trifluoromethyl)benzene (217.2 mg, 0.89 mmol, 1.3 equiv.), NaHCO3 (115.1 mg, 1.37 mmol, 2 equiv.) and DMF (5 mL).The mixture was stirred at 50 °C under air. After the completion of the reaction (monitored by TLC), the reaction mixture was cooled to 21 °C, 5 mL water was added and the mixture was extracted with EtOAC (3*10 mL). The combined organic extracts were...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-VQEGCJLHLB-UHFFFADPSC-NUHFF-NXICJ-NUHFF-ZZZ

Simone Gräßle
(Rp)-1,4(1,4)-dibenzenacyclohexaphane-12-carbaldehyde O-methyl oxime (232 mg, 875 μmol, 1.00 equiv) was added to a solution of 1-bromopyrrolidine-2,5-dione (187 mg, 1.1 mmol, 1.20 equiv), silver trifluoroacetate (38.7 mg, 175 μmol, 0.200 equiv) and palladium(II) acetate (39.3 mg, 175 μmol, 0.200 equiv) in dry 1,2-dichloroethane (17.00 mL) under nitrogen. The reaction was stirred for 3 hours at 100 °C.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-BAIBHOHKSY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
(SP)-1-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)-N-(1-phenylethyl)methanimine (1.42 g, 4.2 mmol, 1.00 equiv) was hydrolyzed by column chromatography on silica gel with methylene chloride.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UIUPXPAOUN-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
Ethyl magnesiumchloride (38.2 mg, 215 μL, 430 μmol, 2.00 equiv) was dissolved in dry THF (7.00 mL) under nitrogen-atmosphere in a Schlenk-flask and (Sp)-3-[2.2]paracyclophanylacetylene (50.0 mg, 215 μmol, 1.00 equiv) was added. The solution was stirred for 15 minutes at 50 °C. The reaction was cooled to room temperature, then 4-methoxyphenyl azide (48.2 mg, 323 μmol, 1.50 equiv) was added. The reaction was heated to 50 °C and stirred for 16 hours at this temperature....

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-BAIBHOHKSY-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
The starting material (S,E)-1-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)-N-(1-phenyl-2-(p-tolyl)ethyl)methanimine (1.33 g, 3.2 mmol, 1.00 equiv) was dissolved in methylene chloride (55.0 mL) and water (750 μL). Acetic acid (788 mg, 750 μL, 13 mmol, 4.10 equiv) was added. The reaction was stirred for 16 hours at room temperature. The layers were separated and the organic phases were washed with 30 mL of 5% HCl solution and water until it was colorless. The organic phase was dried over Na2SO4, filtered and...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-HOTMMJRJOH-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Simone Gräßle
The starting material (148 mg, 430 μmol, 1.00 equiv) was dissolved in THF (6.00 mL) and water (0.6 mL). 4-Toluenesulfonic acid monohydrate (163 mg, 163 μL, 859 μmol, 2.00 equiv) and formaldehyde (339 mg, 311 μL, 4.3 mmol, 10.0 equiv) were added. The reaction was stirred in the microwave for 4 hours at 120°C, 10 bar and 30 Watt.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-DJGWMTKKMO-UHFFFADPSC-NUHFF-NNYHH-NUHFF-ZZZ

Stefan Marschner
To a solution of 933 mg of the porphyrin (1.54 mmol, 1.00 equiv.) in 385 mL CHCl3 were added 0.38 mL pyridine (377 mg, 4.77 mmol, 3.10 equiv.). The mixture was cooled to 0 °C and 646 mg NBS were added, as well as 50 mg in intervals of 30 min respectively, until a complete conversion was observed by TLC (∑ 746 mg, 4.19 mmol, 2.72 equiv.). After addition of the last portion, the reaction...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-LZVFZGBIIF-UHFFFADPSC-NUHFF-NZMGP-NUHFF-ZZZ

Alex Braun
In a vial, 5-iodo-2,2,3-trimethyl-3H-indole (0.325 g, 1.14 mmol, 1.00 equiv.), palladium(II) acetate (25.6 mg, 114.0 μmol, 0.10 equiv.), tetra-n-butylammonium bromide (73.5 mg, 0.228 mmol, 0.20 equiv.) and sodium acetate (0.234 g, 2.85 mmol, 2.50 equiv.) were evacuated and flushed with argon. Then, 1H,1H,2H-perfluoro-1-octene (0.649 mg, 2.85 mmol, 2.50 equiv.) und 7.50 mL dry DMF were added and the reaction mixture was stirred for 20 h at 110 °C. After cooling down, 50 mL ethyl acetate...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-YEYQPMMYRP-UHFFFADPSC-NUHFF-MZOEC-NUHFF-ZZZ

Alex Braun
In a vial, (E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)-3H-indole (110 mg, 272 µmol, 1.00 equiv.) and 77.43 mg methyl iodide (545 µmol, 2.0 equiv.) were dissolved in 0.85 mL acetonitrile and stirred for 20 h at 80 °C.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-GCRYBHUTYS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Sylvia Vanderheiden-Schroen
Under an inert atmosphere, (Rp)-1-bromo-1,4(1,4)-dibenzenacyclohexaphane (200 mg, 695 μmol, 1.00 equiv) was weighed into a dried vial. Dichloropalladium;triphenylphosphane (0.122 g, 0.174 mmol, 0.250 equiv), copper(1+);iodide (0.0265 g, 0.139 mmol, 0.200 equiv) and triphenylphosphane (0.0730 g, 0.278 mmol, 0.400 equiv) were added, the vial was evaporated again and flushed with nitrogen. Then, 5 mL of dry triethylamine and ethynyl(trimethyl)silane (0.478 g, 4.87 mmol, 7.00 equiv) were added, the vial was closed with a crimp cap and...

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