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. 2019 May 22;84(20):13124–13134. doi: 10.1021/acs.joc.9b00878

Table 1. Evaluation of Ligand 1 on Benzylphosphonium Salt 3a.

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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
a

Meta/para ratios are taken from the analysis of crude 1H NMR spectra.

b

Determined by 1H NMR referenced to 1,2-dimethoxyethane as the internal standard.