Table 1.

FLP-mediated hydrogenation of imines.

Entry	Substrate	Solvent	T [°C]	[B] (mol %)	t [h]	Yield [%][a]
1[bc]	2 a	C7H8	80	1 a (10)	22	7
2[bd]	2 a	C7H8	80	1 a (10)	22	99
3	2 a	[D8]THF	60	1 b (5)	3	>99 (98)[e]
4	2 b	[D8]THF	60	1 b (5)	3	>99
5	2 a	THF	60	1 b (5)	3	>99[f]
6	2 c	[D8]THF	60	1 b (5)	8	>99 (99)[e]
7	2 d	[D8]THF	80	1 b (5)	18	71
8	2 e	[D8]THF	60	1 b (15)	8	91
9	2 a	C7D8	60	1 b (5)	3	0
10	2 b	C7D8	60	1 b (5)	3	0
11	2 c	C7D8	60	1 b (5)	8	0
12	2 d	C7D8	80	1 b (5)	18	79
13	2 e	C7D8	60	1 b (15)	8	26
14	2 a	Dioxane	60	1 b (5)	41	96
15	2 a	[D8]THF	60	1 c (5)	72	90
16	2 a	[D8]THF	80	1 a (10)	72	84
17	2 a	[D8]THF	80	1 d (5)	72	0

^[a] Yields measured by in situ ¹H NMR spectroscopy, using 1,3,5-trimethoxybenzene in C₆D₆ in a capillary insert as an internal integration standard.

^[b] Result reported by Klankermayer and Chen.[25a]

^[c] 10 bar H₂.

^[d] 30 bar H₂.

^[e] Number in parentheses is yield isolated after increasing to 1 mmol scale (see Supporting Information).

^[f] Initial reaction mixture prepared using pre-dried solvent under air (see Supporting Information).