Nickel-catalyzed tandem reactions of 3-(2-hydroxy-phenyl)-acrylic acids 1 and 2-iodo-benzenethiols 2, each involving cyclic esterification/C–S bond formationa.
| ||||
|---|---|---|---|---|
| Entry | R | R1 | 3 | Yieldb |
| 1 | H | H |
|
83 |
| 2 | 5-CH3 | H |
|
84 |
| 3 | 5-CH3 | Naphthyl |
|
86 |
| 4 | 4-CH3O | H |
|
89 |
| 5 | 4-CH3O | 4,5-diCH3O |
|
76 |
| 6 | 4-CH3O | Naphthyl |
|
81 |
| 7 | 5-F | H |
|
71 |
| 8 | 5-Cl | H |
|
75 |
| 9 | 5-Br | H |
|
69 |
| 10 | 4,5-diCH3 | H |
|
74 |
| 11 | 4,5-diCH3O | Naphthyl |
|
72 |
Unless otherwise noted, reaction conditions were 1 (0.5 mmol), 2 (0.6 mmol), Ni(CO)4 (10 mol%), NaOEt (2 equiv.), DMSO (5 mL), 90 °C and a reaction time of 10 h.
Isolated yield.