Table 1.

Optimization of one-pot aminobenzylation of benzaldehyde

Entry	Base	Additives	Base: additives (equiv.)	AY (%)a
1	LiN(SiMe3)2	—	3:0	0
2	NaN(SiMe3)2	—	3:0	47
3	KN(SiMe3)2	—	3:0	35
4	NaN(SiMe3)2	CsF	3:3	Trace
5	NaN(SiMe3)2	Cs2CO3	3:3	0
6	NaN(SiMe3)2	CsCl	3:3	0
7	NaN(SiMe3)2	CsOAc	3:3	Trace
8	NaN(SiMe3)2	Cs2SO4	3:3	20
9	NaN(SiMe3)2	CsClO4	3:3	78
10	NaN(SiMe3)2	EtCO2Cs	3:3	17
11	NaN(SiMe3)2	CsBr	3:3	34
12	NaN(SiMe3)2	CsI	3:3	53
13	NaN(SiMe3)2	CsTFA	3:3	92
14	NaN(SiMe3)2	CsTFA	2:3	92
15	NaN(SiMe3)2	CsTFA	2:0.35	95
16	NaN(SiMe3)2	CsTFA	2:0.2	89
17b	NaN(SiMe3)2	CsTFA	1.2:0.35	41
18	LiN(SiMe3)2	CsTFA	2:0.35	94
19	KN(SiMe3)2	CsTFA	2:0.35	50
20c	NaN(SiMe3)2	CsTFA	2:0.35	92
21d	NaN(SiMe3)2	CsTFA	2:0.35	91
22e	NaN(SiMe3)2	CsTFA	2:0.35	67

^aAssay yields (AY) determined by ¹H NMR analysis of crude reaction mixture with CH₂Br₂ as internal standard

^bIn this transformation, 1 equiv. MN(SiMe₃)₂ was needed to form aldimine; the remaining 0.2 equiv. catalyzed the reaction

^cReaction conducted at 80 °C

^dReaction conducted at 40 °C

^eReaction conducted at 30 °C