Synthesis of different derivatives of cinnamic acid (4a–l) through the HCR catalyzed by the Pd@MET-EDTA-CS catalyst (1) under the optimized conditions^a.

Entry	Ar-X	Alkene	Product	Time (h)	Temp. (°C)	Yieldb (%)	TON	TOF (h−1)	m.p. (°C)	m.p. (°C) (Lit.)
1				12	80	90	33 330	2778	131–132	133 (ref. 135)
2				14	80	80	29 630	2116	131–132	133
3				40	80	20	7407	185	131–132	133
4				48	80	Trace	NA	NA	—	212
5				48	80	Trace	NA	NA	—	224–226 (ref. 136)
6				13	80	95	35 185	2706	33–35	34–38 (ref. 137)
7				15	80	85	31 481	2099	33–35	34–38
8				36	80	20	7407	206	—	34–38
9				48	80	Trace	NA	NA	—	34–38
10				48	80	Trace	NA	NA	—	34–38
11				13	80	90	33 330	2564	Liquid	(6.5–7.5) (ref. 138)
12				16	80	80	29 630	1852	Liquid	6.5–7.5
13				36	80	20	7407	206	Liquid	6.5–7.5
14				48	80	Trace	NA	NA	—	—
15				48	80	Trace	NA	NA	—	—
16				15	80	90	33 330	2222	Liquid139	b.p.: 271
17				16	80	85	31 481	1968	Liquid	b.p.: 271
18				36	80	20	7407	206	Liquid	b.p.: 271
19				48	80	Trace	NA	NA	—	—
20				48	80	Trace	NA	NA	—	—

^aReaction conditions: aryl halide (2a–e, 2.0 mmol), alkene (3a–d, 3.0 mmol), K₂CO₃ (2.0 mmol), Pd@MET-EDTA-CS (1, 2.0 mg, 0.0027 mol%), and solvent (3.0 mL), under an Ar atmosphere.

^bIsolated yields.