Skip to main content
. 2019 Aug 7;10:3553. doi: 10.1038/s41467-019-11395-3

Table 1.

Initial optimization of the C–H alkylation of tryptophan 1a

graphic file with name 41467_2019_11395_Figa_HTML.gif
Entry Solvent [1a] T/°C Yield/%
1 GVL/HOAc (1/1) 0.3 m 120 58
2 HO2CEt 0.3 m 120 35
3 HOPiv 0.3 m 120 23
4 HOAc 0.3 m 120 81
5 HOAc 0.3 m 100 88
6 HOAc 0.3 m 80 73
7 HOAc 1.0 m 80 90
8 HOAc 1.0 m 60 80
9 HOAc 1.0 m 37 54
10 HOAc 1.0 m 80 83a
11 HOAc/H2O (3/1) 1.0 m 80 75

Key aspects of C–H alkylation optimization, highlighting acid-enabled C–H activation. Reaction conditions: 1a (0.15 mmol), 2a (0.45 mmol), [RuCl2(p-cymene)]2 (10 mol %), solvent, 15 h

a[RuCl2(p-cymene)]2 (5.0 mol %). 2-py: 2-pyridyl