Table 2. Control experiments of β-lactam formation.
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Entry | Change from the ‘standard conditions’* | Yield of 2d (%)† |
1 | None | 88 |
2 | No Co(OAc)2 | 0 |
3 | Shi’s conditions‡ instead of the standard conditions | 0 |
4 | Co(OAc)2 (1 eq), no Ag2CO3 | 0 |
5 | Ce(SO4)2 (6 eq) instead of Ag2CO3 | 25 |
6 | Co(acac)3 (1 eq) instead of Co(OAc)2, no Ag2CO3 | 0 |
7 | CoF3 (1 eq) instead of Co(OAc)2, no Ag2CO3 | 0 |
8 | Co(acac)3 (10%) instead of Co(OAc)2 | 53 |
9 | CoF3 (10%) instead of Co(OAc)2 | 46 |
10 | Addition of TEMPO (1 eq) | 63 |
11 | Addition of TEMPO (2 eq) | 56 |
*Reaction conditions: 1d (0.3 mmol), Co(OAc)2 (0.03 mmol), Ag2CO3 (0.75 mmol), PhCO2Na (0.15 mmol), 0.6 ml PhCl, 150 °C, 24 h.
†Yields are based on 1d, determined by 1H NMR using dibromomethane as the internal standard.
‡Shi’s conditions: 1d (0.25 mmol), AgOAc (20 mol%), PhI(TFA)2 (0.50 mmol), 4,4′-di-t-butyl-2,2′-bipyridine (20 mol%), K2CO3 (0.50 mmol), PhCl/DCE (1.5 ml/1.5 ml), 120 °C, 12 h.