Skip to main content
. Author manuscript; available in PMC: 2024 Jun 7.
Published in final edited form as: J Am Chem Soc. 2023 May 22;145(22):12377–12385. doi: 10.1021/jacs.3c03587

Table 1. Optimization of reaction conditions for the benzylic amination of 4-ethylanisole.

.

graphic file with name nihms-1897686-t0001.jpg
entry solvent T (°C) variation yielda (%) erb
1 C6H6 rt - 43% 49:51
2 PhCF3 rt - 22% 48:52
3 MeCN rt - 9% 55:45
4 TFE rt - 29% 53:47
5 EtOAc rt - 12% 60:40
6 i-PrOAc rt - 41% 66:34
7 t-BuOAc rt - 13% 61:39
8 i-PrOAc 4 - 56% 71:29
9 i-PrOAc −10 - 14% 65:35
10 i-PrOAc rt no base 34% 65:35
11 i-PrOAc rt 0.5 mol % [Rh] 32% 64:36
a

Determined by 1H NMR in CDCl3 using trimethyl 1,3,5-benzenetricarboxylate as internal standard.

b

Determined by chiral HPLC.