Table 1. Evaluation of Ligand 1 on Benzylphosphonium Salt 3a.
entry | X | ligand | solvent | meta/paraa | % convb |
---|---|---|---|---|---|
1 | OTs | dtbpy | THF | 0 | |
2 | OTs | tmphen | THF | 1:1.3 | 91 |
3 | OTs | 1 | THF | 7:1 | 93 |
4 | Br | 1 | THF | 0 | |
5 | OTs | 1 | dioxane | >20:1 | 100 |
6 | OTs | 1 | CH2Cl2 | >20:1 | 77 |
7 | OTs | 1 | CH3CN | 12:1 | 92 |
8 | OTs | 1 | MTBE | 7:1 | 32 |
9 | OTs | 1 | cyclohexane | 0 | |
10 | OTs | tmphen | dioxane | 1:1.6 | 100 |
Meta/para ratios are taken from the analysis of crude 1H NMR spectra.
Determined by 1H NMR referenced to 1,2-dimethoxyethane as the internal standard.