67 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-LHQKMJBXIU-UHFFFADPSC-NUHFF-NLTSL-NUHFF-ZZZ

Stefan Marschner
Under an Ar atmosphere, 77 mg of porphyrin 14 (101 µmol, 1.00 equiv.), 4 mg CuI (20 µmol, 0.20 equiv.) and 7 mg Pd(PPh3)2Cl2 (10 µmol, 0.10 equiv.) were dissolved in 10 mL of dry THF and 21 mL of dry NEt3. The solution was then purged with Ar gas for 15 min, followed by the addition of 44 µL phenylacetylen (41 mg, 404 µmol, 4.00 equiv.). The reaction was stirred overnight at 25 °C...

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-NRDQBPJLNQ-UHFFFADPSC-NUHFF-NLLDN-NUHFF-ZZZ

Stefan Marschner
To a solution of 39 mg of the porphyrin (51.4 µmol, 1.00 equiv.) in 16 mL of CHCl3 were added 821 mg of copper acetate monohydrate (411 µmol, 8.00 equiv.). The reaction mixture was stirred at 25 °C until complete conversion to copper porphyrin was detected by TLC ( 3 h). Then 430 µL of molecular bromine (1.36 g, 8.48 mmol, 165 equiv.) were added to the reaction mixture directly and the solution was stirred...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-LVGOHACWPD-UHFFFADPSC-NUHFF-NUVBP-NUHFF-ZZZ

Stefan Marschner
Under an Ar atmosphere, 95 mg of the porphyrin (124 µmol, 1.00 equiv.), 265 mg of 3,4,5-(trifluorophenyl)boronic acid (1.51 mmol, 12.2 equiv.), 650 mg of K3PO4 (3.06 mmol, 24.6 equiv.) and 15 mg of Pd(PPh3)4 (13 µmol, 0.10 equiv.) were dissolved in 75 ml of dry THF and the mixture was heated to 80 °C overnight under protection from light. After cooling of the solution to rt the solvent was removed under reduced pressure. The...

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

Stefan Marschner
To a solution of 4.87 g 4-formylbenzoic acid (32.4 mmol, 1.00 equiv.) in 125 mL of DMF were added 8.68 g of K­­2CO3 (62.8 mmol, 1.94 equiv.) and 6.60 mL of iodoethane (12.8 g, 82.1 mmol, 2.54 equiv.). After stirring the reaction for 3 h at 25 °C, water was added, the phases were separated and the aqueous phase was extracted with diethyl ether two times. The combined organic phases were washed with brine, dried...

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

Stefan Marschner
To 340 mL of freshly distilled pyrrole (330 g, 4.92 mol, 92.7 equiv.) were added 1.59 g of paraformaldehyde (53.1 mmol, 1.00 equiv.) and the resulting suspension was stirred for 10 min at 55 °C. Then 1.16 g InCl3 (5.25 mmol, 0.10 equiv.) were added and the resulting mixture was stirred for additional 3 h at 55 °C. After cooling down to rt, 7.02 g of powdered NaOH (176 mmol, 3.31 equiv.) were added and...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-AWGPUPYYXP-UHFFFADPSC-NUHFF-LAXQR-NUHFF-ZZZ

Stefan Marschner
To a solution of 5,15-bis(3,4,5-trimethoxyphenyl)-10,20-bis(4-ethoxycarbonylphenyl)porphyrinato zinc(II) (55.5 mg, 55.4 µmol, 1.00 eq.) in 8 mL of tetrahydrofuran were added 2 mL of methanol and 8 mL of a 40w% solution of NaOH in deionized water (133 mmol, 5.33 g). This mixture was stirred at 90 °C overnight after which the organic solvents were removed under reduced pressure, leaving the product as precipitate in an aqueous suspension. The solid was filtered off and the product was...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ZHQGFWQUTN-UHFFFADPSC-NUHFF-MKELQ-NUHFF-ZZZ

Stefan Marschner
To 5,15-bis(3,4,5-trimethoxyphenyl)-10,20-bis(4-ethoxycarbonylphenyl)porphyrin (65.5 mg, 69.9 µmol, 1.00 eq.) and zinc diacetate (25.6 mg, 0.140 mmol, 2.00 eq.) were added 15 mL of chloroform and 2.5 mL of methanol. The reaction was stirred at 25 °C for 2 h, after which it was diluted with additional chloroform, washed with a saturated aqueous solution of NaHCO3 and water and dried over Na2SO4. After filtration the solvent was removed under reduced pressure and the crude product was filtered...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-JQQMHNZHWI-UHFFFADPSC-NUHFF-NNSBK-NUHFF-ZZZ

Stefan Marschner
5,15-Dibromo-10,20-bis(4-ethoxycarbonylphenyl)porphyrin[4] (153 mg, 0.200 mmol, 1.00 eq.), (3,4,5-trimethoxyphenyl)boronic acid (509 mg, 2.40 mmol, 12.0 eq.), K3PO4 (1.06 g, 5.00 mmol, 25.0 eq) and Pd(PPh3)4 (27.7 mg, 0.024 mmol, 0.12 eq.) were put under an argon atmosphere. The solids were dissolved in a total of 80 mL of dry THF and heated to 75 °C for 18 h. After cooling of the solution to room temperature the THF was evaporated and the residue was dissolved in...

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-NZNGNSDNZK-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Robin Bär
The propellane solution (1.00 mL, 0.52 M in Et2O, 522 μmol, 1.00 equiv) was added to a solution of the 1-methyl-4-[(4-methylphenyl)disulfanyl]benzene (386 mg, 1.6 mmol, 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-FGQYGNNVZD-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Jérôme Klein
4,5-Dimethylbenzene-1,2-diamine (200 mg, 1.5 mmol, 1.00 equiv), benzaldehyde (171 mg, 165 μL, 1.6 mmol, 1.10 equiv) and molecular sieve (20 mg) were dissolved in N,N-dimethylformamide (10.0 mL). The reaction mixture was stirred at 80 °C for 2 h in an open flask and was monitored by TLC. After completion of the condensation, Potassium cyanide (105 mg, 1.6 mmol, 1.10 equiv) was added to the above reaction mixture. On completion of the reaction (overnight), the reaction...

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

Laura Holzhauer
To a solution of 1,2-phenylenediamine (3.02 g, 28 mmol, 1.00 equiv) in THF (50.0 mL) was added methyl 2-oxopropanoate (3.40 g, 3.01 mL, 33 mmol, 1.19 equiv). The solution was then heated to 80 °C for 2 h. After cooling down to room temperature, the formed precipitate was filtered; the remaining solution was reduced by half and filtered again (3x). The solid was then washed with methylene chloride and transferred to a flask. Traces of...

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

Hannes Kühner
In air, a vial equipped with a magnetic stirrer was charged with PEPPSI-IPr catalyst (10mol%) base (1.5 equiv.), 4-bromo-1-oxidopyridin-1-ium (34.8 mg, 200 μmol, 1.00 equiv) and boronic acid (1.20 equiv). The vial was purged with argon three times and solvent (3 mL, iPrOH/water 1:2, degassed) was added by a syringe. The reaction was placed in the microwave reactor and heated for 20 minutes at 150 °C. The reaction mixture was extracted with a Chloroform/iPrOH mixture...

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

Hannes Kühner
To a stirred solution of 4,4'-bipyridine (300 mg, 1.92 mmol, 1.00 equiv) in chloroform (1.00 mL) was added 70% 3-chlorobenzenecarboperoxoic acid (521 mg, 2.11 mmol, 1.10 equiv), portionwise at 0 °C. The resulting mixture was stirred at 21 °C for 23 h, at which time complete consumption of starting material was observed by TLC. The reaction mixture was diluted with chloroform, and solid potassium carbonate (1062 mg, 7,7 mmol, 4,0 equiv) was added. The resulting...

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

Hannes Kühner
A mixture of 4,4'-bipyridine (1.00 equiv) and 4-(bromomethyl)-7-methoxychromen-2-one (1.00 equiv) were dissolved in acetonitrile (3.00 mL) under argon. The solution was then heated up to reflux for 120 min. During the reaction a solid precipitated.

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-XHEOXSQMBW-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Nicole Jung & Simone Gräßle
To a flame-dried 250 mL round-bottemed flask containing crude 1-acetoxy-1,2-benziodoxol-3-(1H)-one (10.6 g, 36 mmol, 1.00 equiv) was added anhydrous cesium;fluoride (138 mg, 910 μmol, 0.0250 equiv), anhydrous acetonitrile (77.0 mL) and trimethyl(trifluoromethyl)silane (7.25 g, 7.53 mL, 51 mmol, 1.40 equiv) successively under inert atmosphere. The reaction mixture was stirred vigorously for 24 h. The white solid suspended in the reaction mixture was then isolated by filtration. This solid was dissolved in 135 mL of chloroform...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ZRNYVIIOMH-UHFFFADPSC-NUHFF-NWIMK-NUHFF-ZZZ

Claudine Herlan
4-Bromoazobenzene (510 mg, 1.50 mmol, 1.00 equiv.), copper(I)-iodide (28.5 mg, 0.150 mmol, 0.100 equiv.), triphenylphosphine (63.0 mg, 0.240 mmol, 0.160 equiv.) and tris(dibenzylideneacetone)-dipalladium(0) (27.5 mg, 0.0300 mmol, 0.0200 equiv.) were mixed and degassed. After addition of 10 mL of dry trimethylamine, the reaction was stirred for 10 min. Trimethylsilylacetylene (368 mg, 3.75 mmol, 2.50 equiv.) was added and the reaction was stirred for 5 days at 90 °C. The solvent was removed and the residue...

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

Claudine Herlan
3-Chloropropylamine hydrochloride (6.00 g, 46.0 mmol, 1.00 equiv) was dissolved in 100 mL of water. Sodium azide (9.00 g, 138 mmol, 3.00 equiv) was added and the mixture was stirred for 18 h at 21 °C. The solvent was reduced to 2/3 of its volume. The remaining mixture was cooled to 0 °C and 100 mL diethylether were added. Potassium hydroxide (6.00 g, 107 mmol, 2.30 equiv.) was added in portions and the organic layer...

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

Alex Braun
A mixture of (4-bromophenyl)hydrazine;hydrochloride (2.00 g, 8.95 mmol, 1.00 equiv.), 3-methyl-2-butanone (2.14 mL, 20.1 mmol, 2.25 equiv.) and 0.46 mL of conc. H2SO4 was dissolved in 32.5 mL of ethanol, heated to 80 °C and stirred for 6 h. After cooling of the reaction mixture to room temperature, the crude product was extracted with dichloromethane. The combined organic phases were washed with NaHCO3 solution and water, dried over Na2SO4 and the solvent was removed under...

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

Hannes Kühner
To a stirred solution of pyridine (1.47 g, 1.50 mL, 19 mmol, 1.00 equiv) in chloroform (9.00 mL) was added 70% 3-chlorobenzenecarboperoxoic acid (4.59 g, 19 mmol, 1.00 equiv), portionwise at 0 °C. The resulting mixture was stirred at room temperature for 12 h, at which time complete consumption of starting material was observed by TLC. The reaction mixture was diluted with chloroform, and solid potassium carbonate (10,3 g, 75 mmol, 4,0 equiv) was added....

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-GCSMQZIBGL-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

Alex Braun
In a vial, iodophenylhydrazine (0.500 g, 1.92 mmol, 1.00 equiv.) and methyl-2-butanone (0.41 mL, 0.331 g, 3.85 mmol, 2.00 equiv.) were dissolved in 7.0 mL of EtOH. After addition of 0.10 mL conc. H2SO4 the mixture was stirred for 12 h at 80 °C. After cooling down, 20 mL of H2O was added to the crude reaction mixture and the product was extracted with 3 × 25 mL of dichloromethane. The combined organic phases were...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UWRWLWRXCL-UHFFFADPSC-NUHFF-NBSLK-NUHFF-ZZZ

Claudine Herlan
Under inert conditions, 4-trimethylsilylethinylazobenzene (340 mg, 1.00 mmol, 1.00 equiv.) was dissolved in 15 mL of dry methanol. After addition of potassium carbonate (163 mg, 1.18 mmol, 1.30 equiv.), the mixture was stirred for 24 h at 21 °C. The precipitated solid was filtered off, washed with water and dried under reduced pressure. The product was obtained as an orange-brown solid in 99% yield (207 mg, 0.900 mmol).

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