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

Entry	Aryl halide	Alkene	Product	t. (min)/NOFb	Conc (%)
1		11a	12a	95/6	90
2		11a	12b	130/8	74
3		11a	12c	130/8	80
4		11a	12d	130/8	85
5		11a	12e	70/5	95
6		11a	12f	70/5	95
7		11a	12g	95/6	90
8		11a	12a	130/8	85
9		11a	12b	130/8	70
10		11a	12c	130/8	72
11		11a	12e	130/8	90
12		11a	12h	95/6	93
13		11a	12a	180/7	Trace
14		11a	12c	180/7	N.R.
15		11a	12e	180/7	50
16		11b	12i	95/6	94
17		11b	12j	107/7	86
18		11b	12k	107/7	80
19		11b	12i	107/7	88
20		11b	12l	95/6	96
21		11b	12i	180/7	30
22		11b	12j	180/7	35
23		11b	12m	180/7	60

^aReaction conditions: Iodobenzene (1.0 mmol), styrene (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 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 yield.