Comparison of Cu–ninhydrin@GO–Ni MNPs in the coupling reaction of chlorobenzene with PhB(OH)₂ with the previously reported procedures.

Entry	Catalyst (mol%)	Aryl halide	Condition	Time (h)	Yield (%)	TOF (h−1)	Ref.
1	Pd(eao)2 (2 mol%)	Chlorobenzene	NaHCO3, PEG400/H2O, 80 °C	360	34	2.8	61
2	Pd NPs@Fe3O4–lignin	Chlorobenzene	K2CO3, EtOH : H2O, 90 °C	270	81	—	62
3	Pd@COF-QA (1.7 mol%)	Chlorobenzene	TEA, H2O, 50 °C	360	99	9.7	63
4	Cross-linked poly(ITC-HPTPy)–Pd (0.23 mol%)	Chlorobenzene	K2CO3, EtOH : H2O, 80 °C	600	96	41	64
5	Pd(dba)2 (2.5 mol%)	Chlorobenzene	Click-triazole, NaOtBu, toluene, 100 °C	18	80	1.8	65
6	Pd–isatin–boehmite (1.48 mol%)	Chlorobenzene	K2CO3, PEG, 80 °C	250	87	14	66
7	Pd(0)TBA@biochar (0.715 mol%)	Chlorobenzene	Na2CO3, PEG, 80 °C	25	89	5	67
8	Pd-imi-CC@MCM-41/Fe3O4 (1.5 mol%)	Chlorobenzene	Na2CO3, PEG, 80 °C	24	89	2.5	68
9	HMS–CPTMS–Cy–Pd	Chlorobenzene	K2CO3, PEG, 100 °C	300	84	12.9	69
10	Cu–MPAMP@Fe3O4	Iodobenzene	Na2CO3, PEG, 80 °C	100	97	51	70
11	Pd/Au NPs (4 mol%)	Iodobenzene	EtOH/H2O, K2CO3, 80 °C	24	88	0.9	71
12	Pd NP (1 mol%)	Iodobenzene	H2O, KOH, 100 °C	12	95	7.9	72
13	Copper powder (10 mol%)	Iodobenzene	K2CO3, PEG, 110 °C	12	99	0.8	73
14	Cu–C (10 mol%)	Iodobenzene	H2O, K2CO3, 50 °C	3.3	96	2.9	74
15	Cu–C (20 mol%)	Chlorobenzene	H2O, K2CO3, 50 °C	240	15	0.2	74
16	Cu–ninhydrin@GO–Ni MNPs (2.12 mol%)	Chlorobenzene	N2CO3, H2O, 80 °C	240	90	10.61	This work
17	Cu–ninhydrin@GO–Ni MNPs (2.12 mol%)	Iodobenzene	N2CO3, H2O, 80 °C	50	97	54.90	This work