Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2821-2828.DOI: 10.6023/cjoc201904058 Previous Articles Next Articles
ARTICLE
收稿日期:
2019-04-24
修回日期:
2019-05-26
发布日期:
2019-06-12
通讯作者:
刘运奎
E-mail:ykuiliu@zjut.edu.cn
基金资助:
Zheng Limeng, Shi Dongdong, Bao Hanyang, Liu Yunkui*()
Received:
2019-04-24
Revised:
2019-05-26
Published:
2019-06-12
Contact:
Liu Yunkui
E-mail:ykuiliu@zjut.edu.cn
Supported by:
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Zheng Limeng, Shi Dongdong, Bao Hanyang, Liu Yunkui. Copper(0)/Selectfluor System-Catalyzed Tandem Annulation/Aromatization of o-Aryl Benzenesulfonylimides:A Facile Synthesis of 6H-Phenanthridines[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2821-2828.
Entry | Catalyst | Oxidant | Solvent | Temp./℃ | Yieldb/% |
---|---|---|---|---|---|
1 | Cu(0) | Selectfluor | MeCNc | 50 | 63 |
2 | Cu(0) | Selectfluor | Anhydrous MeCN | 50 | 15 |
3 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 84 (80)d |
4 | Cu(0) | Selectfluor | MeCN/H2O (V:V=800:1) | 50 | 82 |
5 | Cu(0) | Selectfluor | MeCN/H2O (V:V=250:1) | 50 | 72 |
6 | Cu(0) | Selectfluor | Solvente/H2O (V:V=500:1) | 50 | 0 |
7 | CuI | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 55 |
8 | CuCl | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 63 |
9 | CuBr | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 77 |
10 | Cu2O | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 72 |
11 | CuCl2 | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 47 |
12 | Cu(OAc)2 | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 48 |
13 | — | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 0 |
14 | Cu(0) | — | MeCN/H2O (V:V=500:1) | 50 | 0 |
15 | Cu(0) | NFSIf | MeCN/H2O (V:V=500:1) | 50 | 0 |
16 | Cu(0) | Other oxidantg | MeCN/H2O (V:V=500:1) | 50 | 0 |
17 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 25 | 69 |
18 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 80 | 80 |
19 | Cu(0)h | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 76 |
20 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 46i, 82j |
Entry | Catalyst | Oxidant | Solvent | Temp./℃ | Yieldb/% |
---|---|---|---|---|---|
1 | Cu(0) | Selectfluor | MeCNc | 50 | 63 |
2 | Cu(0) | Selectfluor | Anhydrous MeCN | 50 | 15 |
3 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 84 (80)d |
4 | Cu(0) | Selectfluor | MeCN/H2O (V:V=800:1) | 50 | 82 |
5 | Cu(0) | Selectfluor | MeCN/H2O (V:V=250:1) | 50 | 72 |
6 | Cu(0) | Selectfluor | Solvente/H2O (V:V=500:1) | 50 | 0 |
7 | CuI | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 55 |
8 | CuCl | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 63 |
9 | CuBr | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 77 |
10 | Cu2O | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 72 |
11 | CuCl2 | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 47 |
12 | Cu(OAc)2 | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 48 |
13 | — | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 0 |
14 | Cu(0) | — | MeCN/H2O (V:V=500:1) | 50 | 0 |
15 | Cu(0) | NFSIf | MeCN/H2O (V:V=500:1) | 50 | 0 |
16 | Cu(0) | Other oxidantg | MeCN/H2O (V:V=500:1) | 50 | 0 |
17 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 25 | 69 |
18 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 80 | 80 |
19 | Cu(0)h | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 76 |
20 | Cu(0) | Selectfluor | MeCN/H2O (V:V=500:1) | 50 | 46i, 82j |
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