Table 1 Optimization of reaction conditions for asymmetric dearomative single-atom skeletal editing of benzofuran 1a with diyne 2aa
From: Enantioselective dearomative single-atom skeletal editing of benzofurans
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Entry | L | Reaction conditions | Yield (%)b | Ee (%)c |
1 | L1 | toluene, 35 °C, 14 h | 65 | 16 (+) |
2 | L2 | toluene, 35 °C, 14 h | 79 | 10 (-) |
3 | L3 | toluene, 35 °C, 40 h | 52 | 71 (+) |
4 | L4 | toluene, 35 °C, 15 h | 57 | 68 (+) |
5 | L5 | toluene, 35 °C, 15 h | 50 | 44 (+) |
6 | L6 | toluene, 35 °C, 14 h | 54 | 80 (+) |
7 | L7 | toluene, 35 °C, 15 h | 62 | 72 (+) |
8 | L8 | toluene, 35 °C, 18 h | 70 | 80 (+) |
9 | L9 | toluene, 35 °C, 15 h | 70 | 76 (+) |
10 | L10 | toluene, 35 °C, 19 h | 74 | 88 (+) |
11 | L10 | PhCF3, 35 °C, 15 h | 67 | 85 (+) |
12 | L10 | DCE, 35 °C, 15 h | 75 | 84 (+) |
13 | L10 | THF, 35 °C, 16 h | NR | ND |
14 | L10 | toluene, 15 °C, 44 h | 72 | 90 (+) |
15 | L10 | toluene, 5 °C, 72 h | 62 | 92 (+) |
16d | L10 | toluene, 5 °C, 42 h | 75 | 92 (+) |
