Skip to main content
. Author manuscript; available in PMC: 2021 May 1.
Published in final edited form as: J Org Chem. 2020 Apr 20;85(9):6044–6059. doi: 10.1021/acs.joc.0c00535

Table 2.

Cascade Optimization with Methyl Acrylate

graphic file with name nihms-1593696-t0064.jpg
entry solvent additive % 2ba % 4ba % 5ba
1 DMSO nd 14 77
2 MeOH nd 95 n.d.
3 hexane nd 54 35
4 THF 34 nd 46
5 C6H6 37 nd 11
6 C6H6 AcOH nd 67 nd
7 C6H6 HFIP nd 55 17
8 C6H6 DMAP nd 8 80
9 C6H6 pyridine 5 nd 41
10 C6H6 TEA nd nd 85
11 C6H6 DIPEA nd nd 91
12 PhMe DIPEA nd nd 83
13 THF TEA nd nd 72
14 THF DIPEA nd nd 78
a

Reactions were conducted with azide 1b (70 μmol), methyl acrylate (210 μmol), and an additive (35 μmol) in solvent (0.2 M) at 70 °C. Conversion and yield were determined by calibrated GC-FID analysis. Reactions were run in duplicate, and the average value is reported. Not detected = nd.