Toluene → 8-Phenyl-1,4-dioxa-8-azaspiro[4.5]decane

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,4-dioxa-8-azaspiro[4.5]decane (0.65 mL, 5.0 mmol), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphane) (255 mg, 0.375 mmol), sodium 2-methylpropan-2-olate (1.44 g, 15 mmol), bromobenzene (0.684 mL, 6.5 mmol), tris(dibenzylideneacetone) dipalladium(0) (114 mg, 0.125 mmol) and toluene (15 mL) was stirred at 110° C. for 5 h under Ar atmosphere. Water was added to quench the reaction. The organic materials were extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and filtered. After removal of the solvent at reduced pressure, the residue was purified by column chromatography (Purif, silica gel, 90:10 hexane/EtOAc to 50:50 hexane/EtOAc) to give the title compound (1.09 g, 99%) as an orange oil:

Provenance & Evidence