反应 #2045082

ord-734cbe2005514f718471752ad99bebab

反应方程式

CC(=O)n1c2ccccc2c2cc(-c3cccc(Br)c3)ccc21
1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone
CC1(C)OB(c2cccc(-n3c4ccccc4c4ccccc43)c2)OC1(C)C
9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole
COc1cccc(OC)c1-c1ccccc1P(C1CCCCC1)C1CCCCC1
SPhos
O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
CC(=O)n1c2ccccc2c2cc(-c3cccc(-c4cccc(-n5c6ccccc6c6ccccc65)c4)c3)ccc21
1-(3-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-9H-carbazol-9-yl)ethanone
收率 89.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他the organic solution was isolated
  2. 2
    其他Upon evaporation of the solvent
  3. 3
    其他the residue was purified by column chromatography on silica gel with hexane/DCM (1/1 to 1/4, v/v) as eluent

实验过程

A mixture solution of 1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone (2.50 g, 6.86 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (2.53 g, 6.86 mmol), Pd2(dba)3 (0.063 g, 0.069 mmol), (SPhos) (0.056 g, 0.137 mmol) and K3PO4 (4.74 g, 20.59 mmol) in toluene (180 mL) and water (5 mL) was refluxed under N2 overnight. After cooling to room temperature, the organic solution was isolated. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (1/1 to 1/4, v/v) as eluent to yield 1-(3-(3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-3-yl)-9H-carbazol-9-yl)ethanone (3.2 g, 89%) as a white solid.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08409729B2uspto-grants-2013_04