Reaction #1340562

ord-bed0d9afd4144f1387089f43035b718c

Reaction equation

c1ccc(-c2ccccc2-c2ccccc2)cc1
o-terphenyl
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water
→
c1ccc2c(c1)c1ccccc1c1ccccc21
triphenylene
Yield 35.0%

Reactants

c1ccc(-c2ccccc2-c2ccccc2)cc1
o-terphenyl
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water

Reagents

CC(=O)[O-].CC(=O)[O-].[Pd+2]
Pd(OAc)2

Solvents

CC(=O)N(C)C
DMA

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe reaction mixture is cooled
  2. 2
    Extractionextracted with dichloromethane
  3. 3
    OtherThe organic phase is dried
  4. 4
    Otherthe solvent is removed under reduced pressure
  5. 5
    Otherthe residue is purified by means of a short silica gel column (dichloromethane)

Procedure

2.87 mmol of the o-terphenyl derivative, 0.14 mmol of Pd(OAc)2 and 5.7 mmol of K2CO3 are heated in 7 ml of DMA at 135° C. for 24 hours under a nitrogen atmosphere. The reaction mixture is cooled, treated with 5 ml of water and extracted with dichloromethane. The organic phase is dried, the solvent is removed under reduced pressure and the residue is purified by means of a short silica gel column (dichloromethane). After column chromatography (dichloromethane/hexane, 2:1), the desired triphenylene derivative (IIa) is obtained in from 35 to 40% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08455112B2uspto-grants-2013_06