Table 1.
Comparison of Ni(I) Precatalysts for the Suzuki–Miyaura Reaction of Naphthalen-1-yl Sulfamate and 4-Methoxyphenylboronic Acida
| |||
|---|---|---|---|
| entry | [Ni] | additive | yield |
| 1 | 1 | none | <1% |
| 2 | 1 | (Ph)MgBr | 70% |
| 3 | 1 | (o-tolyl)MgBr | >99% |
| 4 | 1 | (2,6-xylyl)MgBr | 79% |
| 5 | 1 | (2,4,6-mesityl)MgBr | 79% |
| 6 | 1 | (2,4,6-iPr3C6H2)MgBr | 19% |
| 7 | 3 | none | 10% |
| 8 | 3 | TEMPOH | 76% |
a
Reaction conditions: 0.133 mmol naphthalene-1-yl dimethylsulfamate, 0.333 mmol 4-methoxyphenylboronic acid, 0.599 mmol K3PO4, 0.0665 mmol naphthalene (internal standard), 2.5 mol % precatalyst and 2.5 mol % additive, and 1 mL of toluene. Nickel precatalyst was premixed with additive prior to addition of other reagents (see SI). Yields are the average of two runs and were determined by GC.