10.1002/anie.202010840
Angewandte Chemie International Edition
RESEARCH ARTICAL
argon-filled glovebox antechamber. Once transferred inside
the glovebox, KOtBu (22.4 mg, 0.2 mmol) was added to the
vial, followed by freshly prepared catalyst/ligand stock
solution (0.5 mL, 10 mM [Ni] in nPrOH, 0.005 mmol Ni(cod)2,
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0.006
mmol
L19)
(for
anti-Markovnikov-selective
n
hydrofunctionalization) or 0.005 mmol Ni(cod)2 and BuOH
(0.5 mL) (for Markovnikov-selective hydrofunctionalization).
Then, vinyl acetic acid (8.5 µL, 0.1 mmol) was added with a
microsyringe. The vial was sealed with a screw-top septum
cap, removed from the glovebox, and left to stir at 60 °C for
20 h or 48 h. After this time, the reaction was allowed to cool
to room temperature, concentrated under reduced pressure,
then diluted with brine (3 mL) and 2M HCl solution (1 mL).
The aqueous solution was then extracted with ethyl acetate
(3 × 2 mL). The combined organic layers were dried by
passage through a pad of Celite with ethyl acetate as eluent.
The filtrate was concentrated and purified by preparative
thin-layer chromatography (PTLC) to furnish the desired
product.
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