Diphenyl sulfide → Sulfonium, triphenyl-, hexafluoroarsenate(1-) (1:1)

HRID 1732708Notes

Reaction equation

HRID 1732708 reaction equation
[F:1][As-:2]([F:7])([F:6])([F:5])([F:4])[F:3].C1([I+][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)C=CC=CC=1.[C:21]1([S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C([O-])(=O)C1C=CC=CC=1.[Cu+2].C([O-])(=O)C1C=CC=CC=1.[Cu]>[F:1][As-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:28]1([S+:27]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 8766Diphenyl sulfideHCID 2737135Iodonium, diphenyl-, hexafluoroarsenate(1-) (1:1)

Product 1

HCID 93839Sulfonium, triphenyl-, hexafluoroarsenate(1-) (1:1)Yield 97%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 164650Cupric benzoateCatalyst

Procedure

The present invention is based on the discovery that higher yields of aromatic sulfonium salts including substituted derivatives thereof can be obtained at lower reaction temperatures and enhanced reaction rates by employing a copper salt catalyst in combination with the aryl iodonium salt and aryl sulfide or alkyl sulfide. A typical reaction, for example, would be the reaction between diphenyliodonium hexafluoroarsenate and diphenylsulfide in the presence of a copper benzoate catalyst to produce a 97% yield of triphenylsulfonium hexafluoroarsenate at 120° C. for three hours.

Workup

  1. customcan be obtained at lower reaction temperatures
  2. customreaction rates
  3. customA typical reaction

Sources & evidence

ORD record
ord-e591e8e8e7054839b2224420cf7cae3c
Source dataset
uspto-grants-1980_12
Patent number
US04238619

Reaction notes

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