FP@Pd^II-Salen-[IM]OH-catalyzed C–C Sonogashira cross-coupling reaction^a.

Entry	Aryl halide	Product	Time (min)/Cyclesb	Conversionc (%)
1		10a	70/5	96
2		10b	107/7	86
3		10c	107/7	88
4		10d	70/5	96
5		10e	107/7	90
6		10a	110/4	80
7		10b	143/5	75
8		10c	143/5	75
9		10d	80/3	85
10		10f	80/3	85
11		10g	80/3	86
12		10h	80/3	88
13		10a	180/7	50
14		10b	180/7	N.R.
15		10c	180/7	45
16		10f	180/7	60
17		10d	180/7	65

^aReaction conditions: Phenylacetylene (1.0 mmol), iodobenzene (1.0 mmol), EtOH : H₂O (2 : 1, v/v, 5.0 mL), 50 °C (on a water bath), N₂ inlet (0.3 bar; 0.5 bar for aryl bromides, and chlorides), catalytic filter paper (7, placed on a glass funnel, containing 1.0 mmol Pd/95 cm²).

^bTotal time spent in different cycles. Cycles refers to number of re-filtration of the residue (Scheme 2).

^cGC analysis.