Toluene → 2-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiophene

HRID 871122Notes

Reaction equation

HRID 871122 reaction equation
FC(F)(F)S(O[C:7]1[CH:22]=[CH:21][C:10]2[S:11][C:12]3[S:16][C:15]4[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=4[C:13]=3[C:9]=2[CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]3[CH:56]=[CH:55][C:54]4[C:53]5[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=5)[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[C:41]=4[CH:40]=3)[CH:34]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[CH:40]1[C:41]2[C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:48]3[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:54]=2[CH:55]=[CH:56][C:39]=1[C:35]1[CH:34]=[C:33]([C:7]2[CH:8]=[CH:9][C:10]3[S:11][C:12]4[S:16][C:15]5[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=5[C:13]=4[C:21]=3[CH:22]=2)[CH:38]=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 584894164,4,5,5-tetraMethyl-2-(3-(triphenylen-2-yl)phenyl)-1,3,2-dioxaborolaneHCID 86689410HCID 86689410, compound

Product 1

HCID 866894092-(3-(Triphenylen-2-yl)phenyl)benzo[b]benzo[4,5]thieno[3,2-d]thiopheneYield 81.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 962WaterSolvent

Procedure

Benzo[b]benzo[4,5]thieno[3,2-d]thiophen-2-yl trifluoromethanesulfonate (1.5 g, 3.86 mmol), Pd2(dba)3 (0.071 g, 0.077 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.127 g, 0.309 mmol), 4,4,5,5-tetramethyl-2-(3-(triphenylen-2-yl)phenyl)-1,3,2-dioxaborolane (1.82 g, 4.25 mmol), K3PO4 (2.46 g, 11.59 mmol), toluene (90 mL) and water (10 mL) were charged in a 250 mL flask. This mixture was bubbling with nitrogen for 30 minutes then heated up to reflux for overnight. After purification, 1.7 g (81%) of a white solid was obtained. The compound was confirmed by NMR.

Workup

  1. customThis mixture was bubbling with nitrogen for 30 minutes
  2. temperaturethen heated up
  3. temperatureto reflux for overnight
  4. customAfter purification

Sources & evidence

ORD record
ord-1a1f0c484a254789b17a64709f214a98
Source dataset
uspto-grants-2015_03
Patent number
US08969592B2

Reaction notes

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