Table 1.
Screening of reaction conditions. a
| Entry | Variation from ‘standard conditions’ | Yield of 4a (%)b |
|---|---|---|
| 1 | none | 75 |
| 2 | w/o I2 | trace |
| 3 | DMF instead of DMSO | trace |
| 4 | w/o DTBP | 47 |
| 5 | K2S2O8 (2.0 equiv.) instead of DTBP | 19 |
| 6 | PhI(OAc)2 (2.0 equiv.) instead of DTBP | 12 |
| 7 | 70% TBHP (2.0 equiv.) instead of DTBP | 43 |
| 8 | AIBN (2.0) instead of DTBP | 70 |
| 9 | I2 (1.0 equiv.), DTBP (1.0/ 3.0 equiv.) | 72/70 |
| 10 | I2 (0.5/ 2.0 equiv.), DTBP (1.0 equiv.) | 60/57 |
| 11 | At 80/ 120 oC | 59/62 |
aReaction conditions: 1a (1.2 mmol), 2a (1.0 mmol), 3a (1.0 mmol), I2 (1.0 mmol) and DTBP (2.0 mmol) in a solution of DMSO (5.0 mL, c = 0.2 M) at 100 oC for 4 h under air. bIsolated yields.