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CAS No. : | 912331-27-2 | MDL No. : | MFCD08706273 |
Formula : | C9H9BO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 192.04 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.9% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With water; C24H34NP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; gold(I) chloride In 1,2-dichloro-ethane at 20℃; for 24h; | 4.3. General procedure for the hydroarylation of propargylic alcohols with heteroareneboronic acids General procedure: In a 4 mL vial, heteroareneboronic acids (3.equiv., 0.9 mmol), propargylic alcohols (1.0 equiv., 0.3 mmol), and L1AuCl (0.025 equiv., 5.7 mg) were dissolved in DCE (0.84 mL), and NaBARF (0.025 equiv., 6.6 mg) and H2O (0.42 mL) were then added successively. The reaction was stirred at room temperature for 24 h. After completion, AcOEt (30 mL) was added and the reaction mixture was washed with water (10 mL * 3). The organic layer was dried with MgSO4, removed, and the residue was purified with silica gel column chromatograph to afford the corresponding allylic alcohols. The procedure for the synthesis compounds 3x-y is mostly similar to the general procedure except that the reaction was heated at 40 °C for 10 h by using 8% L1AuCl (18.2 mg)/NaBARF (21.1 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | Stage #1: 3-methylbenzothiophene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Triisopropyl borate In tetrahydrofuran at -78 - 20℃; Stage #3: With water; ammonium chloride at 20℃; for 1h; | 4.2.1. Synthesis of compound 1e 3-Methylbenzo[b]thiophene (1.0 equiv., 10 mmol, 1.5 g) was dissolved in anhydrous THF (15 mL) and stirred at -78 °C for about 10 min, and nBuLi (1.2 equiv., 12 mmol, 5.0 mL) was added dropwise to the above solution. After 30 min, B(OiPr)3 (1.5 equiv., 15 mmol, 3.5 mL) was added dropwise and the reaction was slowly warmed up to room temperature. After continually stirred for about 3 h at this temperature, the reaction was quenched with saturated NH4Cl aqueous and further stirred for another 1 h. THF was removed and the residue was dissolved in AcOEt, and washed with H2O. The organic layer was dried with MgSO4 and removed. The crude product was recrystallized by using AcOEt/PE (1:1) to afford compound 1e as white solid. M.p.: 136-138 °C. Yield: 68%. 1H NMR (700 MHz, MeOD) δ 7.83 (d, J = 7.5 Hz, 1H), 7.76 (d, J = 7.4 Hz, 1H), 7.35 (dtd, J = 16.0, 7.2, 1.1 Hz, 2H), 2.52 (s, 3H). 13C NMR (176 MHz, MeOD) δ 143.59, 142.30, 140.13, 125.73, 124.74, 123.18, 123.14, 14.37. HRMS result was not available. |
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