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. 2015 Mar 10;6:6462. doi: 10.1038/ncomms7462

Table 2. Control experiments of β-lactam formation.

Inline graphic
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.