Trimethylphosphine → 4-Methoxybiphenyl

HRID 1786730Notes

Reaction equation

HRID 1786730 reaction equation
CP(C)C.[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:10]([C:11](=N)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14]C=2)=[CH:9][CH:8]=1>[Ni].C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2]>[C:11]1([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:20][CH:19]=2)[CH:12]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 10856767HCID 10856767, compound

Product 1

HCID 119434-MethoxybiphenylYield 1,600%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 9834912Nickel(II) acetylacetonateCatalyst

Procedure

The procedure was identical to Example 1, with the exception that the nickel catalyst used was derived in situ from a combination of anhydrous nickel acetylacetonate (0.026 g; 5 mol %) and trimethylphosphine (0.20 mL of 1 M solution in toluene; 10 mol %). GC analysis of the organic phase of the hydrolyzed reaction sample after 2 h at 60° C. showed the presence of 1.76 mmol (88% yield) of 4-phenylanisole, 0.11 mmol of 4-methoxybenzophenone imine, and no remaining 4-methoxybenzonitrile in the reaction mixture.

Sources & evidence

ORD record
ord-e718b5c472454dc0b21020ceafb9ad37
Source dataset
uspto-grants-2009_03
Patent number
US07507830B2

Reaction notes

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