Table 1. Optimization of Olefin Benzylation Conditions.
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---|---|---|---|---|---|---|---|
entry | R | PR3 | y | x | time (h) |
conv (%)a |
yield (%)a |
1 | H | P(o-anis)3 | 1 atm | 20 | 23 | 76 | 73 |
2 | H | PCyPh2 | 1 atm | 1 | 13 | 100 | 100 |
3 | H | PCyPh2 | 1 atm | 5 | 2 | 100 | 100 |
4 | H | PCyPh2 | 1 atm | 0.5 | 16 | 17 | 17 |
5b | H | PCyPh2 | 1 atm | 20 | 2 | 36 | 1 |
6 | n-hex | PCyPh2 | 5 | 10 | 16 | 59 | 28 |
7 | n-hex | PCy2Ph | 5 | 10 | 16 | 100 | 90 |
8 | n-hex | PCy2Ph | 5 | 5 | 16 | 100 | 80 |
9 | n-hex | PCy2Ph | 2 | 10 | 16 | 100 | 78 |
10 | n-hex | PCy2Ph | 1 | 10 | 16 | 86 | 54 |
Determined by GC.
Et3SiOTf not used.