5692
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amines from readily available aryl chlorides was thus
allowed in good to excellent yield depending on the
substitution pattern of the aryl fragment. Future work
will include efforts to circumvent the use of sodium
hydride to regenerate active Ni species and will be
reported in due course.
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12. Representative procedure for N-phenylmorpholine (3a): In
a Schlenk tube containing degreased NaH (12.2 mmol) in
THF (3 mL) were added Ni(acac)2 (0.2 mmol) and the
dihydroimidazolium chloride 2b (0.8 mmol) and the mix-
ture was heated at 65°C. A solution of morpholine (15
mmol) and t-BuOH (1.2 mmol) in THF (3 mL) was then
added dropwise and the mixture was further stirred at
65°C for 1 h. A solution of chlorobenzene (10 mmol) in
THF (3 mL) was then added and the reaction was
monitored by GC. After complete consumption of the
aryl chloride, the mixture was cooled to room temperature
and adsorbed onto silica gel. The crude reaction mixture
was purified by silica gel column chromatography using
n-hexane–AcOEt (90:10) as eluant to give 3a as a pale
yellow solid. All products in Table 2 have been previously
characterised.
.