Table 1.
entry | deviations | yieldb |
---|---|---|
1 | none | 87% |
2 | TMS3SiH instead of 4 | 15% |
3 | TMS3SiOH instead of 4 | 35% |
4 | no silane source | 0% |
5 | no CuBr | 0% |
6 | no ligand | 0% |
7 | no light | 0% |
8 | no photocatalyst | 0% |
9 | N2 sparge | 0% |
10 | no base | 38% |
Performed with aminosilane reagent 4 (1.8 equiv), NaOAc (4 equiv), aryl bromide 13 (0.1 mmol), and TMSCF3 (3 equiv) in MeCN (0.1 M).
Yields determined by 19F NMR analysis using 1,4-difluorobenzene as internal standard. See SI for more details.