| 99% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; |
|
| 99% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: trimethylsilylacetylene With copper (I) iodide In tetrahydrofuran at 20℃; for 24h; |
|
| 99% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 20 - 70℃; Inert atmosphere; |
|
| 99% |
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With trans-bis(triphenylphosphine)palladium(II) dichloride; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With copper (I) iodide at 50℃; for 2h; Inert atmosphere; |
|
| 99% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; |
1 Example 1: Preparation of 2-(4-methoxynaphthalen-2-yl)aniline (Compound 1)
First, add an appropriate amount to an eggplant-shaped bottle containing o-bromobenzaldehyde (5g, 0.0272mol), bistriphenylphosphine palladium dichloride (0.95g, 0.0014mol), and cuprous iodide (0.50g, 0.0026mol). Oxygen-free and dry tetrahydrofuran, under nitrogen protection, was added trimethylethynyl silicon (6.67 g, 0.0679 mol) and dry triethylamine (19.1 ml, 0.136 mol), and stirring was continued until the terminal alkyne was completely removed consume. After the reaction was completed, the reaction solution was concentrated and subjected to column chromatography to obtain 2-((trimethylsilyl)ethynyl)benzaldehyde with a yield of 99%. |
| 99% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; |
1 Example 1: Preparation of 2-(4-methoxynaphthalen-2-yl)aniline (Compound 1)
First, add an appropriate amount to an eggplant-shaped bottle containing o-bromobenzaldehyde (5g, 0.0272mol), bistriphenylphosphine palladium dichloride (0.95g, 0.0014mol), and cuprous iodide (0.50g, 0.0026mol). Oxygen-free and dry tetrahydrofuran, under nitrogen protection, was added trimethylethynyl silicon (6.67 g, 0.0679 mol) and dry triethylamine (19.1 ml, 0.136 mol), and stirring was continued until the terminal alkyne was completely removed consume. After the reaction was completed, the reaction solution was concentrated and subjected to column chromatography to obtain 2-((trimethylsilyl)ethynyl)benzaldehyde with a yield of 99%. |
| 98% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine for 0.166667h;
Stage #2: trimethylsilylacetylene at 50℃; for 4.5h; |
|
| 98% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene at 50℃; for 4.5h; Inert atmosphere; |
|
| 98% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; |
|
| 98% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere;
Stage #2: trimethylsilylacetylene In N,N-dimethyl-formamide Inert atmosphere; |
|
| 96% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine |
|
| 95% |
With triethylamine In tetrahydrofuran for 4h; Ambient temperature; |
|
| 95% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; |
|
| 95% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h; |
|
| 95% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In triethylamine for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene In triethylamine at 20 - 50℃; for 40h; Sealed tube; |
|
| 95% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran for 5h; |
|
| 94% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In triethylamine at 20℃; for 17h; Inert atmosphere; Schlenk technique; |
|
| 94% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 17h; Inert atmosphere; Schlenk technique; |
|
| 93% |
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) In triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With copper (I) iodide In triethylamine at 50℃; for 16h; Inert atmosphere; |
|
| 93% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran for 0.5h; Inert atmosphere;
Stage #2: trimethylsilylacetylene In tetrahydrofuran for 10h; Reflux; Inert atmosphere; |
1.2 (2) Synthesis of compound represented by [Formula 11]
Was synthesized according to the above Reaction Scheme 2. 6 g of the compound of the formula (10), 31 mg of CuI,119 mg of Pd (PPh3) 2Cl2 was added to the reaction mixture, and the reaction mixture was purged with nitrogen gas. Then, 5 mL of THF and 15 mL of Et3N were added, and the mixture was stirred for 30 minutes. After the completion of the reaction, 5.30 g of trimethylsilyl-acetylene was added, and the mixture was refluxed for 10 hours. After the reaction was completed, the solvent was removed using a vacuum distillation apparatus, and the reaction solvent was extracted with dichloromethane, and then the remaining water was removed using magnesium sulfate.The solvent was removed and the concentrate was purified by silica gel flash chromatography (dichloromethane: hexane = 1: 4) to obtain 6.1 g of a compound of the formula (11) (yield 93%) (FIG. 2). |
| 92% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 45℃; Inert atmosphere; |
|
| 92% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 0 - 45℃; Inert atmosphere; |
|
| 91% |
With palladium diacetate; triphenylphosphine In tetrahydrofuran; hexane; triethylamine at 80 - 90℃; for 5h; |
|
| 91% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; for 16h; Inert atmosphere; |
|
| 90% |
With palladium diacetate; triphenylphosphine In triethylamine at 80℃; for 6h; |
|
| 90% |
With tetrakis-(triphenylphosphine)-palladium; copper atom; potassium carbonate for 17h; Neat (no solvent); |
|
| 90% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; for 16h; Inert atmosphere; |
|
| 90% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 20h; Inert atmosphere; |
|
| 90% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene With copper (I) iodide In tetrahydrofuran at 20℃; Inert atmosphere; |
|
| 89% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran for 12h; Schlenk technique; Inert atmosphere; Reflux; |
|
| 88% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 40 - 50℃; for 1h; |
|
| 88% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide |
|
| 88% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In triethylamine at 65℃; for 16h; |
|
| 88% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; diethylamine In N,N-dimethyl-formamide at 80℃; |
|
| 88% |
With copper (I) iodide; trans-bis(triphenylphosphine)palladium(II) dichloride; triethylamine at 20℃; for 7h; Inert atmosphere; |
|
| 87% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine |
|
| 87% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine for 6h; Reflux; |
|
| 87% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; Inert atmosphere; |
|
| 87% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; |
|
| 86% |
With copper (I) iodide; triethylamine; triphenylphosphine; Palladium(0) bis(dibenzylideneacetone) at 75℃; for 12h; |
|
| 86% |
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With copper (I) iodide at 50℃; Inert atmosphere; |
|
| 85% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; |
|
| 85% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 24h; |
|
| 85% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; |
|
| 85% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene at 50℃; Inert atmosphere; |
|
| 84% |
Stage #1: ortho-bromobenzaldehyde With copper (I) iodide; triethylamine at 23℃; for 0.25h; Inert atmosphere;
Stage #2: trimethylsilylacetylene With tetrakis-(triphenylphosphine)-palladium at 20℃; Inert atmosphere; |
|
| 84% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 100℃; for 2h; Microwave irradiation; |
|
| 84% |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine for 0.25h; Inert atmosphere;
Stage #2: trimethylsilylacetylene at 20℃; for 10h; Inert atmosphere; |
|
| 83% |
Stage #1: ortho-bromobenzaldehyde With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine for 0.166667h;
Stage #2: trimethylsilylacetylene at 25℃; for 8.5h; Inert atmosphere; |
|
| 83% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; |
|
| 82% |
Stage #1: ortho-bromobenzaldehyde In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere of argon;
Stage #2: trimethylsilylacetylene With triethylamine In tetrahydrofuran at 20℃; for 16h; |
1-1
A solution of 2-bromo-benzaldehyde (20.0 g, 108.1 mmol) in anhydrous tetrahydrofuran (200 mL) was degassed with argon for 30 minutes at room temperature. To the above solution was added bis(thphenylphosphine)palladium(ll) chloride (Pd(PPh3^Cb) (3.79 g, 5.4 mmol) and the mixture was degassed again for an additional 15 minutes. To the reaction mixture were added trimethylsilanyl acetylene (33.97 mL, 216.2 mmol), copper(l) iodide (1.0 g, 5.4 mmol) and triethylamine (29.5 ml_, 216.2 mmol), and the mixture was stirred for 16 hours at room temperature. Tetrahydrofuran was removed in vacuo. To the residue was added water (100 ml_), and the resulting mixture was extracted with ethyl acetate (3 x 100 ml_). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a black colored crude product. Flash chromatography (silica gel, 100-200 mesh, 2-5% ethyl acetate in hexane) afforded 2- trimethylsilanylethynyl-benzaldehyde (18.0 g, 82%) as a brown colored solid. MS (ESI+) cald. for Ci2H14OSi [(M+H)+] 202, obsd. 203. |
| 82% |
Stage #1: ortho-bromobenzaldehyde With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine for 0.25h; Inert atmosphere;
Stage #2: trimethylsilylacetylene at 28℃; for 6h; Inert atmosphere; |
|
| 82% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 0 - 45℃; Inert atmosphere; Schlenk technique; |
|
| 81% |
With copper (I) iodide; palladium diacetate; triethylamine; triphenylphosphine at 80℃; for 5h; |
|
| 80% |
With triethylamine In tetrahydrofuran at 25℃; |
|
| 80% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; for 8h; Inert atmosphere; |
|
| 80% |
Stage #1: ortho-bromobenzaldehyde With copper (I) iodide; triethylamine at 23℃; for 0.333333h; Inert atmosphere;
Stage #2: With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) for 0.166667h; Inert atmosphere;
Stage #3: trimethylsilylacetylene at 20℃; for 12h; Inert atmosphere; |
|
| 80% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h; Inert atmosphere; |
a a) Synthesis of 2-((trimethylsilyl)ethynyl)benzaldehyde (S-8)
a) Synthesis of 2-((trimethylsilyl)ethynyl)benzaldehyde (S-8) 2-bromobenzaldehyde (1 g, 5.4 mmol) was added in one portion to a solution of CuI (0.103 g, 10 mol %) in Et3N (20 mL) and degassed with nitrogen for 20 min at 23° C. Pd(PPh3)2Cl2 0.189 g, 5 mol %) was added to the mixture and was stirred for 10 min before being treated with ethynyltrimethylsilane (0.637 g, 6.48 mmol) dropwise. The resulting solution was stirred at room temperature for 12 h and then filtered through a celite pad, concentrated, and eluted through a silica column to give the desired 2-((trimethylsilyl)ethynyl)benzaldehyde (S-8) (0.875 g, 4.32 mmol, 80%). |
| 79% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; |
|
| 79% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; |
|
| 78% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 8.5h; Inert atmosphere; |
|
| 76% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 8h; Inert atmosphere; |
|
| 75% |
With palladium diacetate; triethylamine; triphenylphosphine at 80℃; for 5h; |
|
| 75% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In triethylamine at 20℃; Inert atmosphere; |
|
| 75% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 60℃; for 24h; Inert atmosphere; |
|
| 70% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
|
| 63% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; for 2.5h; Inert atmosphere; |
|
| 55% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; for 3h; Inert atmosphere; |
|
| 50% |
With copper (I) iodide; palladium diacetate; triethylamine; triphenylphosphine at 55℃; for 18h; |
|
| 35% |
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 70℃; Inert atmosphere; |
|
| 33% |
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; for 12h; Schlenk technique; Inert atmosphere; |
|
|
With palladium diacetate; triethylamine; triphenylphosphine for 18h; Heating; |
|
|
With copper (I) iodide; triethylamine In tetrahydrofuran for 4h; Heating; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; |
|
|
With bis(triphenylphosphine)palladium(II) dichloride; triethylamine In acetonitrile for 70h; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; Schlenk technique; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 65℃; for 12h; Inert atmosphere; |
|
|
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: trimethylsilylacetylene In tetrahydrofuran at 80℃; for 5h; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 50℃; Inert atmosphere; |
|
|
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With trans-bis(triphenylphosphine)palladium(II) dichloride; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With copper (I) iodide at 50℃; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h; |
|
|
With copper (I) iodide; bis(triphenylphosphine)palladium(II) chloride; triethylamine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 60℃; for 10h; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 100℃; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran Inert atmosphere; Schlenk technique; Reflux; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 65℃; Inert atmosphere; |
|
|
Stage #1: ortho-bromobenzaldehyde; trimethylsilylacetylene With trans-bis(triphenylphosphine)palladium(II) dichloride; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With copper (I) iodide at 50℃; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 60℃; Inert atmosphere; |
|
|
With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 80℃; for 12h; Inert atmosphere; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; N,N-diisopropylamine In toluene at 50℃; for 16h; |
|
|
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In tetrahydrofuran Inert atmosphere; Reflux; |
|
| 0.96 g |
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: trimethylsilylacetylene With triethylamine at 60℃; for 8h; Inert atmosphere; Schlenk technique; |
|
|
Stage #1: ortho-bromobenzaldehyde With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: trimethylsilylacetylene at 50℃; Inert atmosphere; |
|
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