Tris(1,1-dimethylethyl)phosphine → 9-(dibenzo[b,d]furan-2-yl)-9H-3,9'-bicarbazole

HRID 1514010Notes

Reaction equation

HRID 1514010 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3[CH2:10][CH2:11][CH:12]=[CH:13][C:7]=3[C:6]=2[CH:14]=1.[CH:15]1[C:27]2[N:26]([C:28]3[CH:29]=[CH:30][C:31]4[NH:32][C:33]5[C:38]([C:39]=4[CH:40]=3)=[CH:37][CH:36]=[CH:35][CH:34]=5)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[K]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C(C)=CC=CC=1>[CH:14]1[C:6]2[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=2[CH:4]=[CH:3][C:2]=1[N:32]1[C:31]2[CH:30]=[CH:29][C:28]([N:26]3[C:27]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:20]4[C:25]3=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:40][C:39]=2[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2

Participants

7

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 5462222PotassiumHCID 132360229H-3,9'-BicarbazoleHCID 687356088-Iodo-3,4-dihydrodibenzo[b,d]furan

Product 1

HCID 577031669-(dibenzo[b,d]furan-2-yl)-9H-3,9'-bicarbazoleYield 82.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Procedure

The 100 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with 8-iodo-3,4-dihydrodibenzo[b,d]furan (332 mg, 1 mmol), 3-(9-carbazolyl)carbazole (294 mg, 1 mmol), Pd(OAc)2 (23 mg, 10 mol %), P(t-Bu)3 (1 mL of 1M solution in toluene, 1 mmol), potassium tert-buthoxide (150 mg, 1.5 eq) and 100 ml of xylene. The flask was filled with nitrogen, and the reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 24 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent hexane/ethyl acetate mixture 9:1, providing 410 mg of 9-(dibenzo[b,d]furan-2-yl)-9H-3,9′-bicarbazole as white solid. The structure was confirmed by NMR and MS spectroscopy.

Workup

  1. customThe 100 mL round bottom flask, equipped with magnetic stirrer
  2. temperaturerefluxed condenser
  3. additionThe flask was filled with nitrogen
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux
  6. customThen reaction
  7. filtrationfiltered through silica plug
  8. customevaporated

Sources & evidence

ORD record
ord-21bb7b40c6134599bfc49bf680235ae9
Source dataset
uspto-grants-2012_07
Patent number
US08221905B2

Reaction notes

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