Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4227-4238.DOI: 10.6023/cjoc202304003 Previous Articles Next Articles
ARTICLES
唐朵朵, 黄丹凤*(), 王克虎, 马虎, 冯杨, 任园园, 王君姣, 胡雨来
收稿日期:
2023-04-04
修回日期:
2023-06-05
发布日期:
2023-08-16
基金资助:
Duoduo Tang, Danfeng Huang*(), Kehu Wang, Hu Ma, Yang Feng, Yuanyuan Ren, Junjiao Wang, Yulai Hu
Received:
2023-04-04
Revised:
2023-06-05
Published:
2023-08-16
Contact:
*E-mail: Supported by:
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Duoduo Tang, Danfeng Huang, Kehu Wang, Hu Ma, Yang Feng, Yuanyuan Ren, Junjiao Wang, Yulai Hu. Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4227-4238.
Entry | Molar ratio of 1a∶2a∶Sn | Additive (equiv.) | Solvent | Timeb/h | Yieldc/% | cis∶transd[ |
---|---|---|---|---|---|---|
1 | 1.0∶2.0∶2.5 | None | THF | 12 | 66 | 1.0∶2.4 |
2 | 1.0∶3.0∶3.5 | None | THF | 12 | 56 | 1.0∶1.0 |
3 | 1.0∶1.0∶1.5 | None | THF | 9 | 54 | 1.0∶1.2 |
4 | 1.0∶2.0∶2.5 | In(OTf)3 (0.2) | THF | 6 | 50 | 2.2∶1.0 |
5 | 1.0∶2.0∶2.5 | AgOTf (0.2) | THF | 12 | 67 | 1.0∶2.0 |
6 | 1.0∶2.0∶2.5 | Fe(OTf)3 (0.2) | THF | 7 | 69 | 1.0∶1.5 |
7 | 1.0∶2.0∶2.5 | BF3•Et2O (0.2) | THF | 8 | 58 | 1.6∶1.0 |
8 | 1.0∶2.0∶2.5 | TsOH (0.2) | THF | 8 | 63 | 1.1∶1.0 |
9 | 1.0∶2.0∶2.5 | TfOH (0.2) | THF | 8 | 54 | 1.0∶1.0 |
10 | 1.0∶2.0∶2.5 | H3PO4 (0.2) | THF | 9 | 36 | 1.3∶1.0 |
11 | 1.0∶2.0∶2.5 | HCl (0.2) | THF | 9 | 67 | 1.0∶1.0 |
12 | 1.0∶2.0∶2.5 | HClO4 (0.2) | THF | 5 | 70 | 1.0∶1.2 |
13 | 1.0∶2.0∶2.5 | HClO4 (0.5) | THF | 4 | 78 | 1.4∶1.0 |
14 | 1.0∶2.0∶2.5 | HClO4 (1) | THF | 3 | 53 | 1.8∶1.0 |
15 | 1.0∶2.0∶2.5 | HClO4 (0.5) | Dioxane | 1 | 58 | 1.2∶1.0 |
16 | 1.0∶2.0∶2.5 | HClO4 (0.5) | DCM | 14 | 30 | 1.0∶1.8 |
17 | 1.0∶2.0∶2.5 | HClO4 (0.5) | Toluene | 1 | — | — |
18 | 1.0∶2.0∶2.5 | HClO4 (0.5) | CH3CN | 1 | 53 | 1.0∶1.0 |
19 | 1.0∶2.0∶2.5 | HClO4 (0.5) | EtOH | 1 | 83 | 1.0∶1.1 |
Entry | Molar ratio of 1a∶2a∶Sn | Additive (equiv.) | Solvent | Timeb/h | Yieldc/% | cis∶transd[ |
---|---|---|---|---|---|---|
1 | 1.0∶2.0∶2.5 | None | THF | 12 | 66 | 1.0∶2.4 |
2 | 1.0∶3.0∶3.5 | None | THF | 12 | 56 | 1.0∶1.0 |
3 | 1.0∶1.0∶1.5 | None | THF | 9 | 54 | 1.0∶1.2 |
4 | 1.0∶2.0∶2.5 | In(OTf)3 (0.2) | THF | 6 | 50 | 2.2∶1.0 |
5 | 1.0∶2.0∶2.5 | AgOTf (0.2) | THF | 12 | 67 | 1.0∶2.0 |
6 | 1.0∶2.0∶2.5 | Fe(OTf)3 (0.2) | THF | 7 | 69 | 1.0∶1.5 |
7 | 1.0∶2.0∶2.5 | BF3•Et2O (0.2) | THF | 8 | 58 | 1.6∶1.0 |
8 | 1.0∶2.0∶2.5 | TsOH (0.2) | THF | 8 | 63 | 1.1∶1.0 |
9 | 1.0∶2.0∶2.5 | TfOH (0.2) | THF | 8 | 54 | 1.0∶1.0 |
10 | 1.0∶2.0∶2.5 | H3PO4 (0.2) | THF | 9 | 36 | 1.3∶1.0 |
11 | 1.0∶2.0∶2.5 | HCl (0.2) | THF | 9 | 67 | 1.0∶1.0 |
12 | 1.0∶2.0∶2.5 | HClO4 (0.2) | THF | 5 | 70 | 1.0∶1.2 |
13 | 1.0∶2.0∶2.5 | HClO4 (0.5) | THF | 4 | 78 | 1.4∶1.0 |
14 | 1.0∶2.0∶2.5 | HClO4 (1) | THF | 3 | 53 | 1.8∶1.0 |
15 | 1.0∶2.0∶2.5 | HClO4 (0.5) | Dioxane | 1 | 58 | 1.2∶1.0 |
16 | 1.0∶2.0∶2.5 | HClO4 (0.5) | DCM | 14 | 30 | 1.0∶1.8 |
17 | 1.0∶2.0∶2.5 | HClO4 (0.5) | Toluene | 1 | — | — |
18 | 1.0∶2.0∶2.5 | HClO4 (0.5) | CH3CN | 1 | 53 | 1.0∶1.0 |
19 | 1.0∶2.0∶2.5 | HClO4 (0.5) | EtOH | 1 | 83 | 1.0∶1.1 |
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