Optimization of the reaction conditions^a.

Entry	Variation from “standard conditions”	NMR yield (%)
1	No change	80 (75)b
2	No [Pd(allyl)Cl]2	0
3	No base	0
4	Pd2(dba)3 instead of [Pd(allyl)Cl]2	32
5	SIPr·HCl instead of IPr·HCl	70
6	PCy3 instead of IPr·HCl	40
7	dppp instead of IPr·HCl	0
8	t-BuOLi instead of KOH	54
9	t-BuONa instead of KOH	45
10	t-BuOK instead of KOH	42
11	NaOH instead of KOH	71
12	K3PO4 instead of KOH	30
13	1,4-Dioxane instead of THF	68
14	35 °C instead of 50 °C	41
15	65 °C instead of 50 °C	60

^aReaction conditions: phenyl hydrazone 2a (0.2 mmol, 1.0 M generated in situ from benzaldehyde and hydrazine), 1a (0.1 mmol), [Pd(allyl)Cl]₂ (5 mol%), IPr·HCl (20 mol%), and KOH (1.2 equiv.) in THF (0.2 M) were stirred under N₂ at 50 °C for 16 h. NMR yields were given with mesitylene as the internal standard, and yields were calculated based on 1a.

^bIsolated yield was given in the parentheses.