N-Alkylation of 4-methoxyaniline with benzyl alcohol catalyzed by nickel(ii) complexes^a.

Entry	Complex (mol%)	KOBut (mmol)	Yieldb (%)
1	4 (2.5)	0.4	94
2	4 (1.0)	0.4	84
3	4 (2.5)	0.25	45
4	4 (2.5)	1.0	68
5	—	0.4	Trace
6	4 (2.5)	0.0	0
7c	4 (2.5)	0.4	56
8	3 (2.5)	0.4	91
9	5 (2.5)	0.4	78
10	6 (2.5)	0.4	89

^aClosed tube containing 1 mL of toluene and an oil bath temperature of 140 °C.

^bIsolated yield.

^cKOH as a base.