Toluene → HCID 23137859, compound

HRID 1986342Notes

Reaction equation

HRID 1986342 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.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]>[C:18]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 85532-ChloroanthraquinoneHCID 10796Cesium carbonateHCID 75806TricyclohexylphosphineHCID 4589187Biphenyl-2-boronic acid

Product 1

HCID 23137859HCID 23137859, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Under the atmosphere of argon, 3.4 g (14 mmole) of 2-chloro-anthraquinone, 5 g (17 mmole, 1.2 eq) of 2-biphenylylboronic acid, 0.32 g (0.35 mmole; 5% by mass Pd) of tris(dibenzylideneacetone)dipalladium(0) and 14 g (43 mmole; 2.5 eq) of cesium carbonate were suspended in 40 ml of anhydrous dioxane. Then, 1.1 ml (25% by mass; 0.98 mmole; 1.4 eq to Pd) of a toluene solution of tricyclohexylphosphine was added, and the resultant mixture was stirred at 80° C. for 10 hours.

Sources & evidence

ORD record
ord-3ae61725dc4d48afb29961b7f7ae6ded
Source dataset
uspto-grants-2009_06
Patent number
US07547809B2

Reaction notes

Loading…