Table 1. Screening of Phosphorus-Based Acid Catalystsa.
| entry | catalyst | (mol %) | 1a (%)b | 3aa (%)b | 4aa (%)b |
|---|---|---|---|---|---|
| 1 | (HO)P(O)H2 | 10 | <5 | >95 | <5 |
| 10c | <5c | 79c | 13c | ||
| 5 | <5 | >95 | <5 | ||
| 2 | (HO)2P(O)H | 10 | <95 | <5 | <5 |
| 3 | (HO)3P(O) | 10 | <95 | <5 | <5 |
| 4 | (HO)P(O)(OPh)2B | 10 | <5 | 72 | <5 |
| 5 | <5 | 72 | <5 | ||
| 1 | 14 | 83 | <5 | ||
| 5 | (HO)P(OPh)2 | 10 | <5 | 90 | 5 |
| 5 | 31 | 62 | <5 | ||
| 1 | 70 | 26 | <5 | ||
| 6 | (HO)P(OEt)2A | 10 | <5 | 94 | <5 |
| 5 | 9 | 84 | <5 | ||
| 1 | 47 | 43 | <5 | ||
| 7 | P(OPh)3 | 10 | 5 | 69 | 11 |
| 8 | P(OEt)3 | 10 | <5 | 67 | 11 |
Reaction conditions: 1a (0.5 mmol) and 2a (2 equiv) in technical cumene (0.5 mL).
1H NMR yields/recoveries are the average of two independent experiments and were determined with respect to 1,3,5-trimethoxybenzene as internal standard.
1.5 equiv of 2a.
