Ni/Pd-catalyzed C–C cross-coupling reaction from phenylboronic acid and aldehydes^a.

Entry	R (alcohol or aldehyde)	Product	Time (h)		Yieldb (%)
			From alcohola,c	From aldehyde	From alcohol	From aldehyde
1	H	15a	33	30	84	84
2	4-MeO	15b	36	34	77	79
3	4-Me	15c	36	34	73	75
4	2-Me	15d	32	30	75	75
5	4-CN	15e	28	28	66	60
6	4-NO2	15f	30	30	74	77
7	1-Naphthyl	15g	40	36	70	74
8	4-Cl	15h	35	33	25d	35e
9	2-MeO	15i	36	35	70	70
10	4-NO2, 2-Me	15j	40	36	78	75
11	Nicotine	15k	28	24	80	82
12	Picoline	15l	28	26	82	80
13	2-Furfuryl	15m	40	35	65	80

^aReaction conditions: aldehyde or benzyl alcohol (1.0 mmol), phenylboronic acid (1.0 mmol), catalyst 11 (1.0 mg, 0.013 mol% Pd, 0.034 mol% Ni), DMSO₂ (3.36 g, 35.7 mmol), and 120 °C.

^bIsolated yield.

^cO₂ balloon (∼1.0 atm).

^d45% coupling product was takes place through Cl (major product).

^e33% coupling product was takes place through Cl (major product).