90 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KHVHBJPTOR-UHFFFADPSC-NUHFF-MUHFF-NUHFF-ZZZ

Alex Braun
A mixture of 2,3,3-trimethyl-3H-indole (2.30 g, 14.4 mmol, 1.00 equiv.) and 1-iodo-3-methylbutane (5.72 g, 28.9 mmol, 2.00 equiv.) in 45 mL dry acetonitrile under argon atmosphere were heated to 70 °C and 14 h. The mixture was allowed to cool down to 21 °C and the solvent was removed under reduced pressure. The resulting residue was dissolved in ethyl acetate and the insoluble solid was filtrated.

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-FLHJIAFUWH-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Alex Braun
A mixture of phenylhydrazine (4.00 g, 37.0 mmol, 1.00 equiv.), NaOAc (6.07 g, 74.0 mmol, 2.00 equiv.) and 3-methyl-2-butanone (4.78 g, 55.5 mmol, 1.50 equiv.) in 40 mL acetic acid was heated to 110 °C and stirred for 4 h. After cooling down of the reaction mixture to room temperature the residue was dissolved in dichloromethane. The organic phase was washed with Na2CO3-solution and with NaCl-solution. The organic phase was dried over Na2SO4 and the...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ILXNAEHMTR-UHFFFADPSC-NUHFF-MUHFF-NUHFF-ZZZ

Alex Braun
A mixture of 1-isopentyl-2,3,3-trimethyl-3H-indol-1-ium iodide (400 mg, 1.1 mmol, 1.00 equiv), Vilsmeier-Haack-reagent (181 mg, 0.559 mmol, 1.00 equiv.) and dry NaOAc (275.5 mg, 3.36 mmol, 3.00 equiv.) in 40 mL dry ethanol was refluxed for 2.5 h at 100 °C. After cooling down of the reaction mixture the solvent was removed using reduced pressure. The crude product was dissolved in dichloromethane, washed with 50 mL of water and dried over Na2SO4.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UKPDOEPTPH-UHFFFADPSC-NUHFF-NOHXS-NUHFF-ZZZ

Stefan Marschner & Thomas Wiesner
5-(4-Bromophenyl)-10,15,20-triphenylporphyrin (40.0 mg, 58 μmol, 1.00 equiv) was dissolved in dichloromethane (4 mL) and methanol (1 mL). Cu(OAc)2 (19.2 mg, 106 μmol, 1.83 equiv) was added and the mixture was heated to reflux for 3 h until all starting material was consumed as indicated by TLC. Solvents were evaporated to give a red-purple residue that was taken up in dichloromethane and filtered through a short plug of silica. After filtration, 43.3 mg (57 μmol, 99%...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KZMQSCMPII-UHFFFADPSC-NUHFF-NCYCH-NUHFF-ZZZ

Stefan Marschner & Thomas Wiesner
1.85 g of 4-bromobenzaldehyde (10.0 mmol, 1.00 equiv.), 3.03 mL of benzaldehyde (3.18 g, 30.0 mmol, 3.00 equiv.) and 2.78 mL of pyrrole (2.68 g, 40.0 mmol, 4.00 equiv.) were dissolved in 150 mL of propionic acid. The mixture was heated to reflux for about 1 h, cooled to 25 °C, and around two-thirds of the solvent were removed under reduced pressure. After addition of 40 mL of ethanol, the mixture was cooled overnight in...

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

Stefan Marschner, Thomas Wiesner & Martin Nieger
A Schlenk flask was charged with 130 mg of rac-4-stannyl-[2.2]paracyclophane (261 µmol, 2.24 equiv.), 88 mg of (5‑(4-bromophenyl)-10,15,20-triphenyl-porphyrinato)-copper(II) (116.5 µmol, 1.00 equiv.), 15.3 mg of Pd(PPh3)4 (13.2 µmol 10 mol%), 11.2 mg of LiCl (264 µmol, 2.27 equiv.) and 38.0 mg of CuBr (264 µmol, 2.27 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-MLOTWJWIBH-UHFFFADPSC-NUHFF-NBQDT-NUHFF-ZZZ

Stefan Marschner, Thomas Wiesner & Patrick Weis
A Schlenk flask was charged with 8.30 mg of rac-4,16-dibromo[2.2]paracyclophane (22.7 µmol, 1.00 equiv.), 46.0 mg of (5-(4-stannyl-phenyl)-10,15,20-triphenylporphyrinato)-zinc(II) (47.6 µmol, 2.10 equiv.), 5.3 mg of Pd(PPh3)4 (4.53 µmol 20 mol%),, 2.0 mg of LiCl (45.3 µmol, 2.00 equiv.) and 16.0 mg of CuBr (111 µmol, 5.00 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-VGNCSFRFEF-UHFFFADPSC-NUHFF-NOHXS-NUHFF-ZZZ

Stefan Marschner & Thomas Wiesner
150 mg of 5-(4-bromophenyl)-10,15,20-triphenylporphyrin (216 µmol, 1.00 equiv.) were dissolved in 60 mL of a 10% solution of methanol in chloroform. The reaction was started by the addition of 400 mg of Zn(OAc)2 (2.16 mmol, 10.0 equiv.). The reaction mixture was stirred for 90 min at 25 °C until no starting material was left as indicated by TLC. The crude solution was then washed with water (5 × 30 mL), dried over Na2SO4 and evaporated...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FGNOKQCKXW-UHFFFADPSC-NUHFF-NHKQO-NUHFF-ZZZ

Stefan Marschner & Thomas Wiesner
In an oven-dried 25 mL Schlenk flask under argon atmosphere, 100 mg of (5-(4-bromophenyl)-10,15,20-triphenylporphyrinato)-zinc(II) (132 µmol, 1.00 equiv.), 30.5 mg of Pd(PPh3)4 (26.4 µmol, 0.20 equiv.), 153 mg of hexabutylditin (133 µl, 264 µmol, 2.00 equiv.) and 22 mg of LiCl (520 µmol, 4.00 equiv.) were dissolved in 7 mL of dry toluene. The flask was sealed, and the mixture was stirred for 2 days at 100 °C. After letting the reaction mixture cool down...

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

Daniel Knoll & Stefan Bräse
In a vial fitted with a magnetic stirring bar, potassium 4-trifluoroborate[2.2]paracyclophane (1.50 equiv.), potassium phosphate (4.00 equiv.), palladium acetate (0.05 equiv.), RuPhos (0.15 equiv.) and the respective bromide (1.00 equiv., if solid) 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 (1.00 equiv., if liquid) was added via syringe. The mixture was put into a vial heating block and heated...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-CQICNQVIXS-UHFFFADPSC-NUHFF-NKDHF-NUHFF-ZZZ

Stefan Marschner
Under an Ar atmosphere, 152 mg of the porphyrin (198 µmol, 1.00 equiv.), 287 mg of phenylboronic acid (2.36 mmol, 11.9 equiv.), 1.04 g of K3PO4 (4.91 mmol, 24.7 equiv.) and 27 mg Pd(PPh3)4 (23 µmol, 0.12 equiv.) were dissolved in 45 ml of dry THF and the mixture was heated to 80 °C overnight under protection from light. After cooling of the solution the solvent was removed under reduced pressure. The residue was dissolved...

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-OGJNIRVMBU-UHFFFADPSC-NUHFF-MYXSC-NUHFF-ZZZ

Alex Braun
In a vial, (E)-1,2,3,3-tetramethyl-5-(1H,2H-perfluoroct-1-en-1-yl)-3H-indolium iodide (131 mg, 203 µmol, 1.00 equiv.) and Vilsmeier-Haack salt (32.9 mg, 91.5 µmol, 0.45 equiv.), dissolved in 5.38 mL of dry EtOH and stirred for 2 h at 100 °C under argon atmosphere. After cooling down, 20 mL ethyl acetate was added. The organic phase was washed with 15 mL of water, washed with sat. aqueous NaCl solution and then dried over Na2SO4.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-HUXFCVSRCO-UHFFFADPSC-NUHFF-MYXSC-NUHFF-ZZZ

Alex Braun
In a vial, (E)-1,2,3,3-tetramethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluoronon-1-en-1-yl)-3H-indol-1-ium (75.0 mg, 108 µmol, 1.00 equiv.), sodium acetate (33.4 mg, 406 µmol, 3.77 equiv.) and Vilsmeier-Haack salt (22.3 mg, 62.1 µmol, 0.56 equiv.) were dissolved in 2.85 mL of dry EtOH and stirred for 3 h at 100 °C under an argon atmosphere. After cooling down, 20 mL of ethyl acetate was added. The organic phase was washed with 15 mL of water, washed with sat. aqueous NaCl solution and then...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-WNUUONRSJX-UHFFFADPSC-NUHFF-MYXSC-NUHFF-ZZZ

Alex Braun
In a vial, (E)-1,2,3,3-tetramethyl-5-(3,3,4,4,5,5,6,6,6-nonafluorohex-1-en-1-yl)-3H-indol-1-ium (44.6 mg, 81.8 µmol, 1.00 equiv.), sodium acetate (32.3 mg, 0.393 mmol, 4.81 equiv.) and Vilsmeier-Haack salt (15.9 mg, 49.1 µmol, 0.54 equiv.) were dissolved in 2.58 mL of dry EtOH and stirred for 2 h at 100 °C under argon atmosphere. After cooling down, 20 mL ethyl acetate was added. The organic phase was washed with 15 mL of water, washed with sat. aqueous NaCl solution and then dried over...

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

Alex Braun
In a vial, (E)-2,3,3-trimethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-en-1-yl)-3H-indole (403 mg, 801 µmol, 1.00 equiv.) and methyl iodide (1.137 g, 8.01 mmol, 10.0 equiv.) was stirred for 20 h at 80 °C.

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-ZUUYGWSDFR-UHFFFADPSC-NUHFF-NZMGP-NUHFF-ZZZ

Alex Braun
In a vial, 5-iodo-2,2,3-trimethyl-3H-indole (0.100 g, 0.350 mmol, 1.00 equiv.), 11.8 mg of palladium(II)acetate (52.6 μmol, 0.150 equiv.), 22.6 mg of tetra-nbutylammonium bromide (70.1 µmol, 0.20 equiv.) and 71.9 mg of sodium acetate (0.880 mmol, 2.50 equiv.) were mixed under argon atmosphere. Subsequently 1H,1H,2H-perfluoronon-1-ene (0.350 g, 0.880 mmol, 2.50 equiv.) and 2.30 mL dry DMF were added and the solution was stirred and heated for 20 h at 110 °C. After cooling down, 50 mL...

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

Alex Braun
In a vial, 5-iodo-2,2,3-trimethyl-3H-indole (0.250 g, 0.876 mmol, 1.00 equiv.), palladium(II) acetate (0.0295 g, 131.0 μmol, 0.15 equiv.) and tetra-n-butylammonium bromide (0.0565 g, 0.175 mmol, 0.20 equiv.) were evacuated and backfilled with argon. 0.37 mL of 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (2.19 mmol, 2.50 equiv.) und 5.79 mL of dry DMF were added and the reaction mixture was stirred for 20 h at 110 °C. After cooling down, 50 mL ethyl acetate and 50 mL H20 were added to...

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

Robin Bär
The propellane solution (0.20 mL, 0.53 M in Et2O, 105 μmol, 1.00 equiv) was added to a solution of the 1-phenyl-2-[(2-phenylphenyl)disulfanyl]benzene (117 mg, 316 μmol, 3.00 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-UMLFTCYAQP-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Steven Susanto
To a stirred solution of p-tolunitrile (10.0 g, 85 mmol, 1.00 equiv) in 100 mL of CHCl3 was added NBS (15.6 g, 88 mmol, 1.03 equiv) and benzoyl peroxide (2.07 g, 8.5 mmol, 0.100 equiv). The mixture was stirred at 60 °C over night. The mixture was filtered hot and the solvent was evaporated under reduced pressure.

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

Simone Gräßle
1-Octylindole (250 mg, 1.1 mmol, 1.00 equiv) was dissolved in 10 mL of abs. methylene chloride (N2 atmosphere) and dimethylalumanylium;chloride in hexane (1 M, 1.31 mL, 1.3 mmol, 1.20 equiv) was added at 0 °C. The reaction was stirred for 15 min at 0 °C and 2-phenylacetyl chloride (169 mg, 144 μL, 1.1 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-SPSSDDOTEZ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Laura Holzhauer
Phosphoryl chloride (21.6 g, 13.1 mL, 141 mmol, 20.0 equiv) and 5 mL of DMF were added to the quinoxalinone (1.14 g, 7.0 mmol, 1.00 equiv) and heated to 100 °C for 2 h. The reaction was cooled to 21 °C, poured on ice and rested overnight. The organic phase was separated and the aqueous phase was extracted 3x with ethyl acetate; the combined organic layers were combined were dried over Na2SO4, filtered and the...

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

Alex Braun
A mixture of the indole (0.120 g, 0.217 mmol, 1.00 equiv.) and methyl iodide (42.4 mg, 0.299 mmol, 2.00 equiv.) in 0.68 mL of dry acetonitrile were heated to reflux under argon atmosphere overnight in a vial.

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