Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (9): 2796-2809.DOI: 10.6023/cjoc202403039 Previous Articles Next Articles
ARTICLES
朱洁a, 汤思丹a, 阚秀妹a, 凡士柱a, 王鹏飞a, 杨培俊a,b,*()
收稿日期:
2024-03-26
修回日期:
2024-05-14
发布日期:
2024-05-30
通讯作者:
杨培俊
基金资助:
Jie Zhua, Sidan Tanga, Xiumei Kana, Shizhu Fana, Pengfei Wanga, Peijun Yanga,b()
Received:
2024-03-26
Revised:
2024-05-14
Published:
2024-05-30
Contact:
Peijun Yang
Supported by:
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Jie Zhu, Sidan Tang, Xiumei Kan, Shizhu Fan, Pengfei Wang, Peijun Yang. Solvent-Controlled Sc(OTf)3-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2796-2809.
Entry | Lewis acid (x mol%) | Solvent | T/℃ | t | Yieldb/% | |
---|---|---|---|---|---|---|
3aac | 6a | |||||
1 | Sc(OTf)3 (1) | CH2Cl2 | 25 | 1 min | 95 | 5 |
2 | Cu(OTf)2 (1) | CH2Cl2 | 25 | 1 min | 73 | 6 |
3 | Y(OTf)3 (1) | CH2Cl2 | 25 | 0.2 h | 93 | 7 |
4 | Sm(OTf)3 (1) | CH2Cl2 | 25 | 0.25 h | 88 | 8 |
5 | Eu(OTf)3 (1) | CH2Cl2 | 25 | 0.3 h | 89 | 9 |
6 | Yb(OTf)3 (1) | CH2Cl2 | 25 | 0.15 h | 93 | 7 |
7 | Lu(OTf)3 (1) | CH2Cl2 | 25 | 0.35 h | 94 | 6 |
8 | Sc(OTf)3 (5) | CH2Cl2 | 25 | 1 min | 87 | 13 |
9 | Sc(OTf)3 (1) | ClCH2CH2Cl | 25 | 1 min | 98 | 2 |
10 | Sc(OTf)3 (1) | DMF | 25 | 24 h | NR | NR |
11 | Sc(OTf)3 (1) | DMSO | 25 | 24 h | NR | NR |
12 | Sc(OTf)3 (1) | CH3CN | 25 | 1 min | 32 | 0 |
13 | Sc(OTf)3 (1) | THF | 25 | 4 h | 35 | 65 |
14 | Sc(OTf)3 (1) | Toluene | 25 | 1 min | 90 | 6 |
15 | Sc(OTf)3 (1) | THF | 30 | 2.5 h | 11 | 89 |
16 | Sc(OTf)3 (1) | THF | 35 | 1.5 h | 40 | 60 |
17d | Sc(OTf)3 (1) | THF | 30 | 9 h | — | 88 |
18e | Sc(OTf)3 (0.05) | ClCH2CH2Cl | 25 | 16 h | 94 | 4 |
19f | Sc(OTf)3 (0.1) | THF | 45 | 144 h | — | 90 |
Entry | Lewis acid (x mol%) | Solvent | T/℃ | t | Yieldb/% | |
---|---|---|---|---|---|---|
3aac | 6a | |||||
1 | Sc(OTf)3 (1) | CH2Cl2 | 25 | 1 min | 95 | 5 |
2 | Cu(OTf)2 (1) | CH2Cl2 | 25 | 1 min | 73 | 6 |
3 | Y(OTf)3 (1) | CH2Cl2 | 25 | 0.2 h | 93 | 7 |
4 | Sm(OTf)3 (1) | CH2Cl2 | 25 | 0.25 h | 88 | 8 |
5 | Eu(OTf)3 (1) | CH2Cl2 | 25 | 0.3 h | 89 | 9 |
6 | Yb(OTf)3 (1) | CH2Cl2 | 25 | 0.15 h | 93 | 7 |
7 | Lu(OTf)3 (1) | CH2Cl2 | 25 | 0.35 h | 94 | 6 |
8 | Sc(OTf)3 (5) | CH2Cl2 | 25 | 1 min | 87 | 13 |
9 | Sc(OTf)3 (1) | ClCH2CH2Cl | 25 | 1 min | 98 | 2 |
10 | Sc(OTf)3 (1) | DMF | 25 | 24 h | NR | NR |
11 | Sc(OTf)3 (1) | DMSO | 25 | 24 h | NR | NR |
12 | Sc(OTf)3 (1) | CH3CN | 25 | 1 min | 32 | 0 |
13 | Sc(OTf)3 (1) | THF | 25 | 4 h | 35 | 65 |
14 | Sc(OTf)3 (1) | Toluene | 25 | 1 min | 90 | 6 |
15 | Sc(OTf)3 (1) | THF | 30 | 2.5 h | 11 | 89 |
16 | Sc(OTf)3 (1) | THF | 35 | 1.5 h | 40 | 60 |
17d | Sc(OTf)3 (1) | THF | 30 | 9 h | — | 88 |
18e | Sc(OTf)3 (0.05) | ClCH2CH2Cl | 25 | 16 h | 94 | 4 |
19f | Sc(OTf)3 (0.1) | THF | 45 | 144 h | — | 90 |
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