| 91% |
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; hydroquinone; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 48h; Schlenk technique; Inert atmosphere; |
17 Example 14: Compound 4
General procedure: According to the general method A, the reaction was carried out with 0.3 mmol of arylboronic acid to give 4 (44 mg, yield: 72%).The product was purified by silica gel column chromatography.(n-hexane), a colorless, transparent oil. _: General Method A: Palladium catalyzed difluoromethylation of chlorodifluoroethane and arylboronic acid or ethylene arylborate. Add anhydrous K2CO3 (powder, 4.0 when) to a 25 mL Schlenk back bottle with argon anhydrous and anaerobic protection.Amount), hydroquinone (2.0 equivalents), Pd2 (dba) 3 (2.5 mol%), Xantphos (7.5 mol%) and ArB(OH) 2 (0.3 or 0.5 mmol) or Ar-Beg (0.3 or 0.5 mmol) Level reaction).Then add ClCF2H in 1,4 dioxane solution (2.0M,1.5 mL, 0.3 mmol grade reaction or 2.5 mL, 0.5 mmol grade reaction, 10 equivalents) and freshly distilled 1,4 dioxane (1.0 mL,0.3 mmol level reaction or 2.5 mL, 0.5 mmol level reaction).After the plug was plugged, the reaction mixture was heated to 110 ° C and stirred for 48 hours.After the completion of the reaction, the column chromatography was concentrated to give the object product. |
| 87% |
With 1-methyl-pyrrolidin-2-one; copper(l) iodide; cesium fluoride at 120℃; for 24h; Inert atmosphere; Sealed tube; Glovebox; |
2.2 General Procedure for the Difluoromethylation of Aryl and Vinyl Iodides
General procedure: In a nitrogen-filled glove box, aryl or vinyl iodide (0.5 mmol, 1 equiv), copper iodide (0.5 mmol, 1 eq), and cesium fluoride (1.5 mmol, 1 equiv) were combined in a 20 mL vial. To this vial was added 2.5 mL of anhydrous NMP, followed by trimethyl(difluoromethyl)silane (2.5 mmol, 5 equiv). The reaction mixture was heated in a sealed vessel at 120 °C for 24 h. Note: the pressure increases during the reaction due to the formation of volatile fluorotrimethylsilane (Me3SiF) as a stoichiometric product. The dark red solution was then cooled to room temperature, and diluted with 15 mL of Et20. The mixture was filtered over Celite, washed with an additional 20 mL of Et20, and transferred to a separatory funnel. The mixture was washed with 5 x 20 mL of H20 and 1 x 20 mL of brine, dried with MgS04, filtered, and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with pentane or pentane/Et20 mixtures as the eluent. |
| 84% |
With 1,1'-bis-(diphenylphosphino)ferrocene; N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene silver chloride; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere; |
2
General procedure: Under conditions of argon, 4-phenyliodobenzene was coupled with 2.4 equivalents (2.4 eq) of trimethyldifluoromethylsilane in the presence of 2.0 equivalents of sodium tert-butoxide as the base, The molar ratio of the solvent to the molar ratio of the solvent volume to the molar ratio of the 4-phenyl iodobenzene was added to the molar ratio of the catalyst, the molar ratio of the catalyst was in the range of 10% Ligand dppf, molar ratio of 20% additive SIPrAgCl, 80 ° C, reaction 4 hours, specific for palladium catalyst screening The data are shown in Table 1. |
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