2,2'-Dimethylbiphenyl → 6-(4-Methylphenyl)-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

In a reaction flask was placed NiCl2(dcpb) (38.0 mg, 0.0655 mmol), dcpb (34.6 mg, 0.0768 mmol), tridecane (164.5 mg, 0.892 mmol, as an internal standard), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (169.3 mg, 1.044 mmol). The solvent in the Grignard reagent (1 M in ether, 3.0 mmol) was exchanged with t-AmOMe (5.0 mL) and this solution added to the above catalyst mixture under a nitrogen atmosphere at room temperature. The resulting solution was stirred for several minutes at room temperature and then warmed to 80° C. for 15 hours. A sample was withdrawn and quenched into saturated aqueous ammonium chloride and was extracted with ethyl acetate. GC analysis of the organic phase showed the presence of 6-(4-methylphenyl)-1,2,3,4-tetrahydronaphthalene (0.363 mmol, 35% yield), bitoluene (0.216 mmol), and 6-methoxy-1,2,3,4-tetrahydronaphthalene (0.429 mmol) in the reaction mixture.

Provenance & Evidence