Table 1.
Diazo Decomposition of 19
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Entry | Catalyst | Solvent | Temp (°C) | Time (h) | Product | %Yield |
1 | Rh2(OAc)4 (10 mol %) | benzene | rt | 4 | 20 | 67% |
2 | Rh2(OAc)4 (10 mol %) | benzene | 40 | 1.5 | 20 | 67% |
3 | Rh2(OAc)4 (10 mol %) | benzene | 75 | 2 | 20 | 75% |
4 | CuOTf (80 mol %) | CH2Cl2 | rt | 1 | 18 | 51% |
5 | CuOTf (40 mol %) | CH2Cl2 | reflux | 1 | 18 | 47% |
6 | CuOTf (60–80 mol %) | benzene | rt | 2 | 18 | 51% |
7 | HBF4 (4 - 8 eq.) | CH2Cl2 | rt | > 24 | decomposition | - |
8 | HBF4 (4 - 8 eq.) | CH2Cl2 | reflux | 4 | decomposition | - |
9 | h (λ ≥ 254 nm) | CCl4 | rt | 12 | 19 + baseline | - |