Styrene → HCID 102367693, compound

HRID 926092Notes

Reaction equation

HRID 926092 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+]#N)=[CH:10][CH:9]=1.[CH2:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11](/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7501StyreneHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 102367693HCID 102367693, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

[BMIM][BF4] as Solvent: Palladium(II) acetate (0.5 mg, 0.002 mmol) was added to a solution of 1 (10.5 mg, 0.0330 mmol) and styrene (29.0 mg, 0.278 mmol) in 96.6 mg of [BMIM][BF4]. The mixture was stirred at room temp. for 22 h and was extracted with diethyl ether (0.5 mL×3). The solvent of the combined organic layer was evaporated to give a brown oil, which was purified by SiO2 column chromatography (9:1 hexane/CH2Cl2) to give 2a (2.3 mg, 23% yield) as colorless crystals.

Workup

  1. extractionwas extracted with diethyl ether (0.5 mL×3)
  2. customThe solvent of the combined organic layer was evaporated
  3. customto give a brown oil, which
  4. customwas purified by SiO2 column chromatography (9:1 hexane/CH2Cl2)

Sources & evidence

ORD record
ord-822a29cb232d47c6aa1fd4874bd42f53
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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