Abstract
Nanoporous gold material exhibits a catalytic activity on the
benzannulation reaction between ortho -alkynylbenzaldehydes and
alkynes. The catalyst is easily recoverable and can be reused several
times without leaching and loss of activity.
Key words
nanoporous gold - benzannulation - nanostructures - catalysis - cycloaddition
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15 The catalyst is reusable beyond the
second reuse, but the reaction time tends to be longer for completion,
probably owing to the gradual coarsening of the porous structure.
16
General Procedure
o -alkynylbenzaldehyde 1 (0.2 mmol) and nanoporous gold (20 mol%)
in o -C6 H4 Cl2 (0.5
mL) was added alkyne compound 2 (1.2 mmol)
at r.t. under Ar atmosphere. The mixture was stirred for 2.5 h at
150 ˚C and cooled down to r.t. The liquid moiety
was separated by a pipette and evaporated to leave the crude product,
which was purified by silica gel column chromatography using hexane-EtOAc
as eluent to give the pure product 3 . The
recovered catalyst was washed with Et2 O several times,
dried under reduced pressure, and reused without further purification.
