Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1216-1223.DOI: 10.6023/cjoc202009014 Previous Articles Next Articles
ARTICLES
孙扬阳a, 冯刚b, 陈超a, 刘永红a,*(), 张旭a,*()
收稿日期:
2020-09-06
修回日期:
2020-09-29
发布日期:
2020-10-22
通讯作者:
刘永红, 张旭
基金资助:
Yangyang Suna, Gang Fengb, Chao Chena, Yonghong Liua,*(), Xu Zhanga,*()
Received:
2020-09-06
Revised:
2020-09-29
Published:
2020-10-22
Contact:
Yonghong Liu, Xu Zhang
About author:
Supported by:
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Yangyang Sun, Gang Feng, Chao Chen, Yonghong Liu, Xu Zhang. Gram-Scale Synthesis of Polymeric Carbon Nitride-Supported Copper: A Practical Catalyst for Ullmann-Type C—N Coupling Modifying Secondary Pyrimidin-2-amines without Additional Ligand[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1216-1223.
Entry | Solvent | Base | T/℃ | Yieldb/% |
---|---|---|---|---|
1 | t-BuOH | t-BuOK | 80 | 23 |
2 | EtOH | t-BuOK | 80c | 20 |
3 | THF | t-BuOK | 80c | 22 |
4 | 1,4-Dioxane | t-BuOK | 80 | 28 |
5 | Toluene | t-BuOK | 80 | 16 |
6 | 1,4-Dioxane | KOH | 80 | 20 |
7 | 1,4-Dioxane | NaOH | 80 | 16 |
8 | 1,4-Dioxane | Pyridine | 80 | 18 |
9 | 1,4-Dioxane | t-BuOK | 90 | 45 |
10 | 1,4-Dioxane | t-BuOK | 100 | 67 |
11 | 1,4-Dioxane | t-BuOK | 110c | 82 |
12 | 1,4-Dioxane | t-BuOK | 120c | 80 |
13d | 1,4-Dioxane | t-BuOK | 110c | 44 |
Entry | Solvent | Base | T/℃ | Yieldb/% |
---|---|---|---|---|
1 | t-BuOH | t-BuOK | 80 | 23 |
2 | EtOH | t-BuOK | 80c | 20 |
3 | THF | t-BuOK | 80c | 22 |
4 | 1,4-Dioxane | t-BuOK | 80 | 28 |
5 | Toluene | t-BuOK | 80 | 16 |
6 | 1,4-Dioxane | KOH | 80 | 20 |
7 | 1,4-Dioxane | NaOH | 80 | 16 |
8 | 1,4-Dioxane | Pyridine | 80 | 18 |
9 | 1,4-Dioxane | t-BuOK | 90 | 45 |
10 | 1,4-Dioxane | t-BuOK | 100 | 67 |
11 | 1,4-Dioxane | t-BuOK | 110c | 82 |
12 | 1,4-Dioxane | t-BuOK | 120c | 80 |
13d | 1,4-Dioxane | t-BuOK | 110c | 44 |
Entry | Ar | X | R | 3 | Yieldb/% |
---|---|---|---|---|---|
1 | Ph | I | Me | 3a | 82 |
2 | 4-FC6H4 | I | Me | 3b | 60 |
3 | 4-ClC6H4 | I | Me | 3c | 90 |
4 | 4-BrC6H4 | I | Me | 3d | 72 |
5 | 4-MeC6H4 | I | Me | 3e | 88 |
6 | 3,4-(Me)2C6H3 | I | Me | 3f | 65 |
7 | 4-MeOC6H4 | I | Me | 3g | 80 |
8 | 3-MeOC6H4 | I | Me | 3h | 80 |
9 | 2-MeOC6H4 | I | Me | 3i | 75 |
10 | 4-PhC6H3 | I | Me | 3j | 65 |
11 | 2-C10H7 | I | Me | 3k | 98 |
12 | | I | Me | 3l | 92 |
13 | 4-(4-IC6H4)C6H4 | I | Me | 3m | 60 |
14 | 4-MeOC6H4 | I | PhCH2c | 3n | 53 |
15 | Ph | Br | Me | 3a | 56, 60d |
16 | 4-ClC6H4 | Br | Me | 3c | 68d |
17 | 4-MeC6H4 | Br | Me | 3e | 52d |
18 | Ph | Cl | Me | 3a | 26, 30d |
Entry | Ar | X | R | 3 | Yieldb/% |
---|---|---|---|---|---|
1 | Ph | I | Me | 3a | 82 |
2 | 4-FC6H4 | I | Me | 3b | 60 |
3 | 4-ClC6H4 | I | Me | 3c | 90 |
4 | 4-BrC6H4 | I | Me | 3d | 72 |
5 | 4-MeC6H4 | I | Me | 3e | 88 |
6 | 3,4-(Me)2C6H3 | I | Me | 3f | 65 |
7 | 4-MeOC6H4 | I | Me | 3g | 80 |
8 | 3-MeOC6H4 | I | Me | 3h | 80 |
9 | 2-MeOC6H4 | I | Me | 3i | 75 |
10 | 4-PhC6H3 | I | Me | 3j | 65 |
11 | 2-C10H7 | I | Me | 3k | 98 |
12 | | I | Me | 3l | 92 |
13 | 4-(4-IC6H4)C6H4 | I | Me | 3m | 60 |
14 | 4-MeOC6H4 | I | PhCH2c | 3n | 53 |
15 | Ph | Br | Me | 3a | 56, 60d |
16 | 4-ClC6H4 | Br | Me | 3c | 68d |
17 | 4-MeC6H4 | Br | Me | 3e | 52d |
18 | Ph | Cl | Me | 3a | 26, 30d |
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