Methanol → 3-Phenylcycloheptanone

Participants

Reaction Conditions

Reaction Steps

Next, the scope of boronic acids that can be utilized was briefly examined. More specifically, the general experimental procedure for the 1,4-addition of arylboronic acids to enones will be described using 2-cyclohexen-1-one and phenylboronic acid. A mixture of 2-cyclohexen-1-one (96 mg, 1 mmol) and phenylboronic acid (158 mg, 1.3 mmol) was taken in a round bottom flask. A toluene solution (3 ml) containing Rh(acac)(CO)2 (5 mg, 0.02 mmol) and JanaPhos (70 mg, 0.03 mmol, Rh/P=1/3) was added to it in an inert atmosphere. A solution of methanol and water (1:1, 0.5 ml) was added to it via syringe. The reaction mixture was heated at 50° C. for 15 hours until the starting material was consumed as indicated by TLC. Then 25 ml methanol was added to it mixture and the catalyst was precipitated out as a white solid. It was filtered out by a Schlenk filter and underwent for the consecutive runs. The filtrate was evaporated under reduced pressure to obtain the crude product which was further purified by column chromatography (10% ethyl acetate in hexane) to obtain the pure product (144 mg, 83% yield).

Provenance & Evidence