Table 1. Screening of Representative Catalyst Systemsa.
entry | ligand (L) | 2 | 3 | 4b |
---|---|---|---|---|
1 | none | 3 | 85 | 12 |
2 | TMEDA (1.1 equiv) | 83 | 8 | 9 |
3 | TMEDA (0.1 equiv) | 11 | 76 | 13 |
4 | PPh3 | 16 | 82 | 2 |
5 | P(o-Tol)3 | 10 | 90 | 0 |
6 | DPEPhos | 65 | 25 | 10 |
7 | DPEPhos/TMEDA | 90 | 8 | 2 |
8 | 1,2-di-PPh2-C6H4 | 0 | 79 | 21 |
9 | 1,2-di-PPh2-C6H4/TMEDA | 50 | 50 | 0 |
10 | dtbpf | 91 | 7 | 2 |
11 | dtbpf/TMEDA | 94 | 6 | 0 |
Conditions: 0.3 mmol of alkenyl halide substrate (0.25 M in THF). Palladium catalyst (2 mol %), Grignard reagent (1.75 equiv), TMEDA (1.85 equiv).
GC ratio.