The control experiments for the domino oxidation Suzuki–Miyaura cross-coupling of benzyl alcohol with phenylboronic acid^a and domino reduction C–N cross-coupling of nitrobenzene with iodobenzene^b.

Entry	Catalyst	15a	19a
		Conversion (%)	Conversion (%)
1	Catalyst 10	40	80
2	Polyvinyl chlorophyll-Pd(ii) (13)	N.R.	Trace
3	Chlorophyll b	N.R.	N.R.
4	Fe3O4	N.R.	N.R.
5	Fe3O4@SiO2	N.R.	N.R.
6	Fe3O4@SiO2–NH2	N.R.	N.R.
7	Compound 5	25	65
8c	Catalyst 10-poisoned	N.R.	N.R.
9c	Catalyst 11-poisoned	5	N.R.
10	Catalyst 11	4d	—
11e	5/Fe3O4@SiO2–NH2/Ni(OAc)4·H2O	35	30

^aReaction conditions: benzyl alcohol (1.0 mmol), phenylboronic acid (1.0 mmol), catalyst (1.0 mg), DMSO₂ (3.36 g, 35.7 mmol), 120 °C, O₂ balloon (∼1.0 atm), 33 min.

^bReaction conditions: nitrobenzene (1.0 mmol), iodobenzene (1.0 mmol), catalyst (2.0 mg), NaBH₄ (2.0 mmol), DMSO₂ (3.36 g, 35.7 mmol), 120 °C, 4.2 h.

^cHg(0) was added equal to 320 molar equivalents vs. Pd content.

^dThe preparation of 15a was performed under an N₂ (sealed) atmosphere.

^e5 (1.0 mg), Fe₃O₄@SiO₂–NH₂ (2.0 mg), Ni(OAc)₄·H₂O (0.1 mg).