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[ CAS No. 22445-41-6 ]

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2D
Chemical Structure| 22445-41-6
Chemical Structure| 22445-41-6
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Product Details of [ 22445-41-6 ]

CAS No. :22445-41-6MDL No. :MFCD00060659
Formula : C8H9I Boiling Point : 229.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :232.06Pubchem ID :140924
Synonyms :

Computed Properties of [ 22445-41-6 ]

TPSA : 0 H-Bond Acceptor Count : 0
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.25 Rotatable Bond Count : 0

Safety of [ 22445-41-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22445-41-6 ]

  • Upstream synthesis route of [ 22445-41-6 ]
  • Downstream synthetic route of [ 22445-41-6 ]

[ 22445-41-6 ] Synthesis Path-Upstream   1~18

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  • [ 461-97-2 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 26, p. 10795 - 10798
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  • [ 556-96-7 ]
Reference: [1] Journal of the American Chemical Society, 2002, vol. 124, # 50, p. 14844 - 14845
[2] Patent: WO2004/13094, 2004, A2, . Location in patent: Page 88
[3] Patent: WO2004/13094, 2004, A2, . Location in patent: Page 88
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  • [ 172975-69-8 ]
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YieldReaction ConditionsOperation in experiment
77% With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
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  • [ 499-06-9 ]
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YieldReaction ConditionsOperation in experiment
58% With N-iodo-succinimide; [4,4’-bis(tert-butyl)-2,2’-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate; iodine; caesium carbonate In 1,2-dichloro-ethane at 50℃; for 24 h; Inert atmosphere; Irradiation; Sealed tube General procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), Niodosuccinimide(NIS) (0.9 mmol, 202.5 mg) and I2 (15 μmol, 5 molpercent) were added. The tube was evacuated and backfilled with argon for three times, and then 3 mL of dry 1,2-dichloroethane(DCE) was added through a syringer under argon. The tube was sealed with Parafilm M® andplaced in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C underirradiation with 6 × 5 W blue LEDs (λmax = 455 nm). After 24 or 36 h, the resulting mixture wasfiltered through a 2 cm thick pad of silica, and the silica was washed with dichloromethane (DCM)(50 mL). The filtrate was collected and the solvent was removed in vacuo. The crude residue waspurified by silica gel flash column chromatography to provide the target product (2). (Note: Thereaction was very sensitive to moisture, and the yields sharply decreased to less than 5percent when0.01 equivalent of H2O was added to the reaction system).
Reference: [1] Synlett, 2018, vol. 29, # 12, p. 1572 - 1577
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  • [ 108-69-0 ]
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Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 1, p. 116 - 119
[2] Monatshefte fuer Chemie, 1934, vol. 64, p. 361,364, 365[3] Monatshefte fuer Chemie, 1935, vol. 65, p. 6,14
[4] Journal of Organic Chemistry, 1974, vol. 39, p. 2546 - 2552
[5] European Journal of Organic Chemistry, 2016, vol. 2016, # 33, p. 5529 - 5538
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  • [ 556-96-7 ]
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YieldReaction ConditionsOperation in experiment
78 - 98 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In toluene at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.; A Schlenk tube was charged with CuI, sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [N, NAPOS;-DIMETHYLETHYLENEDIAMINE,] 5- [BROMO-M-XYLENE] (136 [UL,] 1.00 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 22 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, [230 GEL)] were added to the reaction mixture. A 50 pL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
71 %Chromat. With N-butylethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
73 %Chromat. With trans-1,2-Diaminocyclohexane; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
< 0.1 %Chromat. With sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
22 %Chromat. With 1,1-dimethylethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
< 0.1 %Chromat. With triphenylphosphine; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
52 %Chromat. With Trimethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
69 %Chromat. With Trimethylenediamine; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
69 %Chromat. With ethylenediamine; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
4 %Chromat. With 1,10-Phenanthroline; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
70 %Chromat. With sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
96 %Chromat. With sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
8 %Chromat. With 1,3-bis(methylamino)propane; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
20 %Chromat. With N,N-dimethylethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
71 %Chromat. With sodium iodide; N-methyl-ethane-1,2-diamine In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
60 %Chromat. With N-ethylethane-1,2-diamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
95 %Chromat. With (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
1 %Chromat. With (2-hydroxyethyl)(methyl)amine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
98 %Chromat. With trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
22 %Chromat. With rac-trans-N,N'-diethyl-1,2-cyclohexanediamine; sodium iodide In 1,4-dioxane at 110℃; for 22 h; Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL,] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL,] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.
99 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In sulfolane at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
99 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In 1,4-dioxane at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
49 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In 1-methyl-pyrrolidin-2-one at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
99 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In tert-Amyl alcohol at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
49 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In α,α,α-trifluorotoluene at 110℃; for 23 h; A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1,] 2-cyclohexanediamine (16 [ILL,] 0.10 mmol, 10 [MOLpercent),] 5-bromo-m- xylene [(136 GEL,] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.
30 %Chromat. With 3-azapentane-1,5-diamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
18 %Chromat. With N,N',N'-trimethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.
14 %Chromat. With (R,R)-1,2-diphenylethylenediamine; sodium iodide In 1,4-dioxane; dodecane at 110℃; for 22 h; Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.

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YieldReaction ConditionsOperation in experiment
1.4g With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 7 h; Inert atmosphere To the stirred solution of 1-iodo-3, 5-dimethyl benzene (2.0 g, 8.61 mmol) in 40 mlanhydrous DMF (degassed by argon) was added LiC1 (1,80 g, 43.00 mmol), Pd(dba)3 (98.6mg, 0.11 mmol), EtNPr2 (2.95 ml, 17.23 mmol) and acetic anhydride (2.5 ml). The flask was degassed by argon and the mixture was stirred for 7 h at 100 °C. The reaction was monitoredby TLC and after completion of the reaction, mixture was cooled and then subjected to a standard ether work up to give 1.4 g of the desired product as a liquid and was used for the next step without purification as NIVIR and mass show desired compound has formed.
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