Table 1:
entry | Fe (a mol%) | ligand (b mol%) | disulfide (c mol%) | Na2CO3 (d mol%) | yield of 2 (%) |
---|---|---|---|---|---|
1 | 2.5 | 2.5 | 5 | 10 | 95 |
2 | 1 | 1 | 5 | 10 | 88 |
3 | 0.5 | 0.5 | 5 | 10 | 59 |
4 | - | 2.5 | 5 | 10 | 4 |
5 | 2.5 | 2.5 | - | 10 | 6 |
6[b] | 2.5 | 2.5 | 5 | 10 | 25 |
7 | 2.5 | 2.5 | 5 | - | 38 |
8[c] | 2.5 | 2.5 | 5 | 10 | 53 |
9[d] | 2.5 | 2.5 | 5 | 10 | N.R. |
10[e] | 2.5 | 2.5 | 5 | 10 | 77 |
11 | 2.5 | - | 5 | 10 | 72 |
12 | 2.5 | - | 15 | 10 | 81 |
All reactions were conducted on a 0.4 mmol scale and the yields were determined by 1H NMR spectroscopy using trimethoxybenzene as an internal standard. TRIP disulfide = Bis(2,4,6-triisopropylphenyl) disulfide.
Diphenyl disulfide was used instead of TRIP disulfide.
427 nm LED light was used instead of 390 nm light.
No light; N.R. = no reaction.
DCE (0.1 M) was used as the solvent; Trace amount of α,β-unsaturated ketone was observed.