Potassium Carbonate → Trans-2-(2-(Trifluoromethyl)Cyclopropyl)Naphthalene

Participants

Reaction Conditions

Reaction Steps

In an open vial with pressure-release top, a stirred mixture of 2-naphthyltrifluoromethanesulfonate (Aldrich, St. Louis, Mo.) (69 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (23 mg, 0.05 mmol), K2CO3 (138 mg, 1.0 mmol) and trans-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H2O (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100° C. and stirred for 6 hours. After allowing to cool, the reaction mixture was diluted with H2O (15 mL) and EtOAc (20 mL), filtered through Celite and the filter cake washed with EtOAc (2×20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (2 prep TLC plates used) using EtOAc/hexane (1:99) as eluent to give the product (45.9 mg, 78%) as a solid.

Provenance & Evidence