478 Works

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-ALURCEXFHY-UHFFFADPSC-NUHFF-LUHFF-NUHFF-ZZZ

Jasmin Busch & Olaf Fuhr
A 20 mL crimp vial was charged with (4-tert-butylpyridin-2-yl)-diphenylphosphane (224 mg, 701 μmol, 1.00 equiv), tris(4-fluorophenyl)phosphane (444 mg, 1.40 mmol, 2.00 equiv) and copper(1+);iodide (267 mg, 1.40 mmol, 2.00 equiv) under argon. 12 mL of dry DCM (SPS-system) were added under argon and the suspension was degassed with argon for 5 min. The reaction mixture was stirred over night at 25 °C for 15 h. The yellow solution was reduced to 4 mL and was...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-YQLAZYJXUL-UHFFFADPSC-NUHFF-LUHFF-NUHFF-ZZZ

Jasmin Busch & Olaf Fuhr
A 20 mL crimp vial was charged with [4-(cyclopentylmethyl)pyridin-2-yl]-diphenylphosphane (276 mg, 799 μmol, 1.00 equiv), triphenylphosphane (419 mg, 1.60 mmol, 2.00 equiv) and copper(1+);iodide (152 mg, 799 μmol, 1.00 equiv) under argon. 12 mL dry DCM (SPS-system) were added under argon and the suspension was degassed with argon for 5 min. The reaction mixture was stirred over night at 25 °C for 15 h. The yellow solution was reduced to 4 mL and was poured...

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

Yannick Matt & Isabelle Wessely
Under an argon atmosphere, 5-iodo-2-$l^{1}-oxidanyl-1,1,3,3-tetramethylisoindole (3.03 g, 9.58 mmol, 1.00 equiv), copper(1+);iodide (23.0 mg, 121 μmol, 0.0126 equiv) and [Pd(PPh3)2Cl2] (151 mg, 215 μmol, 0.0224 equiv) were placed in 10 mL of degassed triethylamine. Then, ethynyl(trimethyl)silane (1.93 g, 2.80 mL, 19.7 mmol, 2.05 equiv) was added and the reaction mixture was stirred at 50 °C for 6 h. After cooling to room temperature, the precipitate was filtered off and the solvent removed under reduced pressure....

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

Jérôme Klein
Oxalic acid;dihydrate (1.35 g, 10.7 mmol, 1.10 equiv) was added to a solution of 1,2-phenylenediamine (1.05 g, 9.71 mmol, 1.00 equiv) in aqueous HCl (2.92 g, 20.0 mL, 80.0 mmol, 4.00M, 8.24 equiv), and the resulting solution was stirred at 110 °C for 2 h. The reaction mixture was cooled to 21 °C and the resulting precipitate was filtered, washed with water, and dried.

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

Helena Šimek
To a stirred solution of 2-iodoaniline (250.0 mg, 1.14 mmol, 1.0 equiv.) and pyridine (186.2 mg, 0.19 mL, 2.35 mmol, 2.1 equiv.) in CH2Cl2 (2.5 mL) was added p-toluenesulfonyl chloride (261.7 mg, 1.37 mmol, 1.2 equiv.) at 0 °C. The reaction was stirred at 0 °C for 1 h, and then allowed to warm to 21 °C and stir until the complete consumption of starting material (monitored by TLC, 4 h). The reaction mixture was...

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

Jérôme Klein
2,3-Dimethylquinoxaline (2.00 g, 13 mmol, 1.00 equiv),1-bromopyrrolidine-2,5-dione (5.63 g, 32 mmol, 2.50 equiv) and benzoyl benzenecarboperoxoate (408 mg, 1.3 mmol, 0.100 equiv) were dissolved in acetonitrile (50.00 mL) and stirred at 90 °C for 7 h. The solution was then allowed to reach 21 °C. Methylene chloride and distilled water were then added and the aqueous layer was extracted 3x with methylene chloride. The organic layers were combined and dried over Na2SO4. The solvent was...

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

Isabelle Wessely
1-[4-(1-Hydroxyethyl)phenyl]ethanol (3.58 g, 21.5 mmol, 1.00 equiv) was dissolved in 150 mL of dichloromethane at 0 °C, before hydron bromide (14.2 g, 10.0 mL, 57.9 mmol, 2.69 equiv) was added. After the reaction was stirred for 3.5 h at this temperature, 70 mL water were added. The phases were separated and the organic phase was washed with a saturated NaHCO3-solution, water and brine before being dried over sodium sulfate. The solvent was removed under reduced...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-XHFJIHLNMP-UHFFFADPSC-NUHFF-LUHFF-NUHFF-ZZZ

Jasmin Busch & Olaf Fuhr
A 20 mL crimp vial was charged with (4-methyl-2-pyridyl)-diphenyl-phosphine (500 mg, 1.80 mmol, 1.00 equiv), tris(4-fluorophenyl)phosphane (1.14 g, 3.61 mmol, 2.00 equiv) and copper(1+);iodide (687 mg, 3.61 mmol, 2.00 equiv) under argon. 15 mL dry DCM (SPS-system) were added under argon and the suspension was degassed with argon for 5 min. The reaction mixture was stirred over night at 25 °C for 15 h. The yellow solution was poured dropwise on 300 mL of n-pentane.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-PDIAHQRNBM-UHFFFADPSC-NUHFF-LUHFF-NUHFF-ZZZ

Jasmin Busch
A 20 mL crimp vial was charged with diphenyl(pyridin-2-yl)phosphane (184 mg, 700 μmol, 1.00 equiv), tris[4-(trifluoromethyl)phenyl]phosphane (653 mg, 1.40 mmol, 2.00 equiv) and copper(1+);iodide (267 mg, 1.40 mmol, 2.00 equiv) under argon. 14 mL dry DCM (SPS-system) were added under argon and the suspension was degassed with argon for 5 min. The reaction mixture was stirred over night at 25 °C for 15 h. The yellow solution was reduced to 4 mL and was poured...

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

Simon Oßwald
Methyl 3-[1,2-dihydroxy-2-(3-methoxycarbonylphenyl)ethyl]benzoate (200 mg, 605 μmol, 1.00 equiv) and N-Bromosuccinimide (323 mg, 1.82 mmol, 3.00 equiv) were dissolved in dry CHCl3 (10 mL). The solution was refluxed in an oil bath maintained at 70°C for 1.5 hours. After cooling to room temperature, the reaction was quenched with aq. Na2S2O3 (10 mL) and the organic layer was separated. The aqueous layer was extracted with CHCl3 (2×10 mL). The combined organic layers were dried over anhyd. MgSO4,...

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

Simon Oßwald
N,N′‐Bis(4-(methoxycarbonyl)-2,6-dimethylphenyl)ethylenediimine (200 mg, 526 μmol, 1.00 equiv), chloromethyl ethyl ether (0.5 mL) and MeCN (2mL) were combined under an argon atmosphere at room temperature. The reaction mixture was heated to 100 °C for 5 hours. When the determined time was reached, the solution was cooled to room temperature, solvent was removed under vacuum and the reaction mixture was treated with ethyl acetate to precipitate the product. The solid was isolated by filtration and washed three...

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

Lukas Langer
The S-phenyl-S-bicyclo[1.1.1]pentylsulfoximine (50 mg, 241 µmol, 1.00 equiv.), Cu2O (6.9 mg, 48.2 µmol, 20 mol%) and KOtBu (54 mg, 482 µmol, 2.00 equiv.) were mixed in a dry vial under argon atmosphere. Then, dimethylformamide (DMF) (0.5 mL), 1-iodo-2-methoxybenzene (47 µL, 85 mg, 362 µmol, 1.50 equiv.) and 1,2-dimethylethylenediamine (DMEDA) (5.2 µL, 4.2 mg, 48.2 µmol, 20 mol%) were added. The mixture was stirred at 100 °C for 18 h. After cooling to 21 °C, the...

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

Lukas Langer
The sulfoximine (50 mg, 241 µmol, 1.00 equiv.), Cu2O (6.9 mg, 48.2 µmol, 20 mol%) and KOtBu (54 mg, 482 µmol, 2.00 equiv.) were mixed in a dry vial under argon atmosphere. Then, dimethylformamide (DMF) (0.5 mL), 1-iodo-3-methoxybenzene (43 µL, 85 mg, 362 µmol, 1.50 equiv.) and 1,2-dimethylethylenediamine (DMEDA) (5.2 µL, 4.2 mg, 48.2 µmol, 20 mol%) were added. The mixture was stirred at 100 °C for 18 h. After cooling to 21 °C, the...

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

Lukas Langer
The S-phenyl-S-bicyclo[1.1.1]pentylsulfoximine (50 mg, 241 µmol, 1.00 equiv.), 1-chloro-4-iodobenzene (86 mg, 362 µmol,1.50 equiv.), Cu2O (6.9 mg, 48.2 µmol, 20 mol%) and KOtBu (54 mg, 482 µmol, 2.00 equiv.) were mixed in a dry vial under argon atmosphere. Then, dimethylformamide (DMF) (0.5 mL) and 1,2-Dimethylethylenediamine (DMEDA) (5.2 µL, 4.2 mg, 48.2 µmol, 20 mol%) were added. The mixture was stirred at 100 °C for 18 h. After cooling to rt, the mixture was diluted with...

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

Lukas Langer
S-phenyl-S-bicyclo[1.1.1]pentylsulfoximine (50 mg, 241 µmol, 1.00 equiv.), 1-iodo-4-methylbenzene (79 mg, 362 µmol, 1.50 equiv.), Cu2O (6.9 mg, 48.2 µmol, 20 mol%) and KOtBu (54 mg, 482 µmol, 2.00 equiv.) were mixed in a dry vial under argon atmosphere. Then, dimethylformamide (DMF) (0.5 mL) and 1,2-dimethylethylenediamine (DMEDA) (5.2 µL, 4.2 mg, 48.2 µmol, 20 mol%) were added. The mixture was stirred at 100 °C for 18 h. After cooling to rt, the mixture was diluted with...

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

Lukas Langer
S-phenyl-S-bicyclo[1.1.1]pentylsulfoximine (50 mg, 241 µmol, 1.00 equiv.), Cu2O (6.9 mg, 48.2 µmol, 20 mol%) and KOtBu (54 mg, 482 µmol, 2.00 equiv.) were mixed in a dry vial under argon atmosphere. Then, dimethylformamide (DMF) (0.5 mL), 1-iodo-3-methylbenzene (47 µL, 79 mg, 362 µmol, 1.50 equiv.) and 1,2-dimethylethylenediamine (DMEDA) (5.2 µL, 4.2 mg, 48.2 µmol, 20 mol%) were added. The mixture was stirred at 100 °C for 18 h. After cooling to 21 °C, the mixture...

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

Robin Bär
BCP-SO2Na (123 mg, 0.795 mmol, 1.30 equiv.), 2-chloroquinoline (100 mg, 0.611 mmol, 1.00 equiv.) and potassium carbonate (127 mg, 0.917 mmol, 1.50 equiv.) were mixed in a dry vial under argon atmosphere. DMF (1.0 mL) was added and the mixture was stirred at 120 °C for 16 h.

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

Lukas Langer & Martin Nieger
To a stirred solution of 1-[(4-tert-butylphenyl)thio]bicyclo[1.1.1]pentane (37.0 mg, 159 μmol, 1.00 equiv.) in methanol (3.00 mL) was added ammonium carbonate (30.6 mg, 318 μmol, 2.00 equiv.), followed by (diacetoxyiodo)benzene (154 mg, 478 μmol, 3.00 equiv.). After stirring for 30 min at 21 °C the solvent was removed under reduced pressure.

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

Robin Bär & Martin Nieger
BCP-SO2Na (142 mg, 0.921 mmol, 1.30 equiv.) and 1-fluoro-4-nitrobenzene (75 µL, 100 mg, 0.709 mmol, 1.00 equiv.) were mixed in a dry vial under argon atmosphere. DMF (1.0 mL) was added and the mixture was stirred at 80 °C for 3 d.

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

Robin Bär
Methyl 3-(bicyclo[1.1.1]pentan-1-ylsulfonyl)propanoate (13.3 g, 61 mmol, 1.00 equiv.) was dissolved in tetrahydrofuran (130 mL) and stirred at 21 °C. Sodium methanolate (3.29 g, 11.3 mL, 5.4 M, 61 mmol, 1.00 equiv.) was added to the solution and a pale yellow solid precipitated. After complete addition the reaction mixture was stirred at 21 °C for 20 min. The solvent and the formed acrylate were evaporated under reduced pressure. The product was obtained as a pale yellow...

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

Janina Beck
In a crimp vial under argon atmosphere, N-(4-bromo-3-(1,4-dioxo-1,4-dihydronaphthalene-2-carbonyl)phenyl)-2,2,2-trifluoroacetamide (181 mg, 400 µmol, 1.00 equiv.) was dissolved in dry CH2Cl2 (4 mL) and 2,3-dimethylbuta-1,3-diene (0.14 mL, 98.6 mg, 1.20 mmol, 3.00 equiv.) was added. The reaction was stirred at 40 °C for 5 h until the consumption of the dienophile was completed as indicated by TLC.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-FOIXCRBFVL-UHFFFADPSC-NUHFF-NLYQR-NUHFF-ZZZ

Janina Beck
In a crimp vial under argon atmosphere, 2‑(2‑bromo­benzoyl)­naphthalene-1,4-dione (273 mg, 800 µmol, 1.00 equiv.) was dissolved in dry CH2Cl2 (4.0 mL) and (buta-1,3-dien-2-yloxy)(tert-butyl)diphenylsilane (1.3 mL, 1.23 g, 4.00 mmol, 5.00 equiv.) was added. The reaction was stirred at 40 °C for 5 h. The solvent was removed under reduced pressure.

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-UMSRHQGWSN-UHFFFADPSC-NUHFF-NHVYL-NUHFF-ZZZ

Janina Beck
In a crimp vial under argon atmosphere 2‑(2‑iodobenzoyl)naphthalene-1,4-dione (200 mg, 515 µmol, 1.00 equiv.) was dissolved in dry CH2Cl2 (7.0 mL) and (E)‑tert-butyldimethyl((2-methylbuta-1,3-dien-1-yl)oxy)silane (512 mg, 2.58 mmol, 5.00 equiv.) was added. The reaction was stirred at 40 °C for 6 h. The solvent was removed under reduced pressure.

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

Janina Beck
To a solution of (4aR,9aR)-2-((tert-butyldiphenylsilyl)oxy)-4a-(2-iodobenzoyl)-1,4,4a,9a-tetrahydroanthracene-9,10-dione (44.6 mg, 64.0 µmol, 1.00 equiv.) in a mixture of dry MeOH and dry CH2Cl2 (1:1) (0.4 mL) was added a drop of AcCl (50 μL, 55.3 mg, 700 µmol, 11 equiv.) at 0 °C and the reaction mixture was stirred for 3.5 h at this temperature. After completion of the reaction (monitored by TLC), CH2Cl2 was added (4.0 mL), the reaction mixture was neutralized with 10% NaHCO3 (0.5 mL)...

Short-RInChIKey=SA-FUHFF-UHFFFADPSC-TZBXDZKIGZ-UHFFFADPSC-NUHFF-NDRCZ-NUHFF-ZZZ

Janina Beck
A suspension of 3-sulfolene (5.00 g, 42.0 mmol, 16.4 equiv.) in o‑xylene (15 mL) was heated to 125 °C for 0.5 h. The thereby developed gaseous 1,3‑butadiene was led into a reaction vessel containing a solution of 2‑(2-iodobenzoyl)naphthalene-1,4-dione (1.00 g, 3.00 mmol, 1.00 equiv.) in CH2Cl2 (5.0 mL) at –78 °C. After completion of the evolution of 1,3‑butadiene gas, the mixture of dienophile and diene in CH2Cl2 was slowly warmed to 21 °C and stirred...

Registration Year

  • 2020
    478

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  • Workflow
    478