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Suzuki-Miyaura coupling reaction of potassium aryl trifluoroborate using palladium(II) acetate; 4-methoxybiphenyl

SyntheticPage 948
Submitted Feb 15, 2021, published Mar 01, 2021
Takuya Miura (Takuya.Miura@TCIchemicals.com), Yuko Konishi (Yuko.Konishi@tcichemicals.com)


			Reaction Scheme: Suzuki-Miyaura coupling reaction of potassium aryl trifluoroborate using palladium(II) acetate

Chemicals Used

potassium phenyltrifluoroborate (TCI-P1582, used as received)
4-bromoanisole (TCI-B0547, used as received)
palladium(II) acetate (TCI-P2161, used as received)
potassium carbonate
methanol
water
dichloromethane
hydrochloric acid (2mol/L)
brine
anhydrous sodium sulfate
silica-gel
n-hexane
ethyl acetate

Procedure

 Potassium phenyltrifluoroborate (500 mg, 2.72 mmol), potassium carbonate (1.13 g, 8.15 mmol), and palladium(II) acetate (3 mg, 0.014 mmol) were added to solution of 4-bromoanisole (509 mg,2.72 mmol) in methanol (10 mL) at rt under N2 atmosphere. After reflux for 2 h, the reaction mixture was cooled to rt, quenched by addition of water (20 mL), and extracted with dichloromethane (30 mL×2). Obtained organic phase was washed with 2N HCl aq. (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate and filtered. After solvent was removed under reduced pressure, crude was purified by column chromatography (silica-gel, n-hexane:EtOAc = 20:1) to give 4-methoxybiphenyl (380 mg,76%) as a white solid.

Author's Comments

All chemical manipulations were performed in a fume hood. 
Methanol was used as reaction solvent without degassing operation.
Consumption of stating material and formation of product were monitored by TLC(n-hexane:AcOEt = 20:1). Rf: 0.625(4-bromoanisole), 0.50(4-methoxybiphenyl).
This procedure is typical for Suzuki-Miyaura coupling using organotrifluoroboates.

Data

1H NMR (400 MHz, CDCl3); δ 7.51–7.56 (m, 4H), 7.39–7.44 (m, 2H), 7.28–7.32 (m, 1H), 6.96–6.99 (m, 2H), 3.85 (s, 3H).

Lead Reference

G. A. Molander and B. Biolatto, J. Org. Chem. 2003, 68, 4302. (DOI: https://doi.org/10.1021/jo0608366)

Supplementary Information

1H NMR.pdf

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Get structure file (.cdx, .sk2, .mol)

Keywords: alkyl/alkenyl/aryl halides, aromatics/arenes, cross coupling, transition metal catalysed

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