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. Author manuscript; available in PMC: 2021 Aug 6.
Published in final edited form as: Tetrahedron Lett. 2020 Jul 3;61(32):152196. doi: 10.1016/j.tetlet.2020.152196

Table 2.

Reductive amination of benzaldehydesa

graphic file with name nihms-1610118-t0003.jpg
Entry Aldehyde 2 (%)b 3 (%)b 4 (%)b
1 1a R = H 81 (72c) <1 18
2 1b R = p-OMe 79 (92c) <1 21
3 1c R = p-Br 87 (73c) 2 11
4 1d R = m-Br 72 (84c) 7 21
5 1e R = o-Br 97 (89c) 3 <1
6 1f R = p-Cl 98 (90c) <1 <1
7 1g R = p-F 48 26 26
8 1h R = p-NO2 87(81c) 4 9
9 1i R = m-NO2 86 4 10
10 1j R = o-NO2 71 8 21
11 1k R = p-CN 63 9 28
a

Reagents and conditions: aldehyde (100 μmol), Ir1 (1.0 μmol), HCOONH4 (1.0 mmol), CH3OH (0.5 mL), 37 °C, 15 h.

b

Determined by 1H NMR with 1,3,5-trimethoxybenzene as internal standard, each experiment was performed in triplicate and the average yield was calculated.

c

Isolated yield. Some isolated yields of 2 were higher than their NMR yields because compound 4 was hydrolyzed to 2 during the workup step.