有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1607-1613.DOI: 10.6023/cjoc202008035 上一篇 下一篇
研究论文
成立1, 王文蓉1, 孙玉倩1, 李团结1,* ltj2008@jsnu.edu.cn., 于晨侠1, 姚昌盛1,*()
收稿日期:
2020-08-20
修回日期:
2020-10-13
发布日期:
2020-12-24
通讯作者:
李团结, 姚昌盛
基金资助:
Li Cheng1, Wenrong Wang1, Yuqian Sun1, Tuanjie Li1,* ltj2008@jsnu.edu.cn., Chenxia Yu1, Changsheng Yao1,*()
Received:
2020-08-20
Revised:
2020-10-13
Published:
2020-12-24
Contact:
Tuanjie Li, Changsheng Yao
About author:
Supported by:
文章分享
在氮杂环卡宾(NHC)/银(I)的共催化下, 以芳醛和(溴乙炔)苯及其衍生物为原料实现了2-氧代-2-芳乙基芳甲酸酯高效合成. 该方法具有底物范围广、原料简单易得、操作简便等优点, 为α-酰氧基羰基衍生物的简捷合成提供了新思路.
成立, 王文蓉, 孙玉倩, 李团结, 于晨侠, 姚昌盛. 氮杂环卡宾(NHC)/银(I)共催化合成2-氧代-2-芳乙基芳甲酸酯[J]. 有机化学, 2021, 41(4): 1607-1613.
Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.
Entry | NHC | Base | Solvent | T/℃ | Yieldb/% |
---|---|---|---|---|---|
1 | 4 | K2CO3 | DCM | 80 | 10 |
2 | 5 | K2CO3 | DCM | 80 | 0 |
3 | 6 | K2CO3 | DCM | 80 | 45 |
4 | 7 | K2CO3 | DCM | 80 | 60 |
5 | 7 | K2CO3 | K2CO3 | 80 | 52 |
6 | 7 | K2CO3 | K2CO3 | 80 | 15 |
7 | 7 | K2CO3 | K2CO3 | 80 | 14 |
8 | 7 | K2CO3 | K2CO3 | 80 | 8 |
9 | 7 | K3PO4 | DCM | 80 | 52 |
10 | 7 | DBU | DCM | 80 | 0 |
11 | 7 | DABCO | DCM | 80 | 0 |
12 | 7 | Cs2CO3 | DCM | 80 | 10 |
13 | 7 | K2CO3 | DCM | 30 | 0 |
14 | 7 | K2CO3 | DCM | 40 | 10 |
15 | 7 | K2CO3 | DCM | 50 | 47 |
16 | 7 | K2CO3 | DCM | 60 | 59 |
17 | 7 | K2CO3 | DCM | 70 | 70 |
Entry | NHC | Base | Solvent | T/℃ | Yieldb/% |
---|---|---|---|---|---|
1 | 4 | K2CO3 | DCM | 80 | 10 |
2 | 5 | K2CO3 | DCM | 80 | 0 |
3 | 6 | K2CO3 | DCM | 80 | 45 |
4 | 7 | K2CO3 | DCM | 80 | 60 |
5 | 7 | K2CO3 | K2CO3 | 80 | 52 |
6 | 7 | K2CO3 | K2CO3 | 80 | 15 |
7 | 7 | K2CO3 | K2CO3 | 80 | 14 |
8 | 7 | K2CO3 | K2CO3 | 80 | 8 |
9 | 7 | K3PO4 | DCM | 80 | 52 |
10 | 7 | DBU | DCM | 80 | 0 |
11 | 7 | DABCO | DCM | 80 | 0 |
12 | 7 | Cs2CO3 | DCM | 80 | 10 |
13 | 7 | K2CO3 | DCM | 30 | 0 |
14 | 7 | K2CO3 | DCM | 40 | 10 |
15 | 7 | K2CO3 | DCM | 50 | 47 |
16 | 7 | K2CO3 | DCM | 60 | 59 |
17 | 7 | K2CO3 | DCM | 70 | 70 |
Entry | R | Ar | Time/h | Product | Yield/% |
---|---|---|---|---|---|
1 | 4-ClC6H4 | C6H5 | 12 | 3a | 70 |
2 | 4-BrC6H4 | C6H5 | 12 | 3b | 68 |
3 | 4-FC6H4 | C6H5 | 12 | 3c | 58 |
4 | 3-BrC6H4 | C6H5 | 12 | 3d | 65 |
5 | 3,4-Cl2C6H3 | C6H5 | 12 | 3e | 75 |
6 | 4-O2NC6H4 | C6H5 | 12 | 3f | 74 |
7 | 4-CH3OC6H4 | C6H5 | 24 | 3g | 48 |
8 | Thiophene-2-yl | C6H5 | 12 | 3h | 58 |
9 | 3,4-Cl2C6H3 | 4-ClC6H4 | 12 | 3i | 73 |
10 | 4-ClC6H4 | 4-ClC6H4 | 12 | 3j | 68 |
11 | 4-NO2C6H4 | 4-ClC6H4 | 12 | 3k | 76 |
12 | 4-CH3OC6H4 | 4-ClC6H4 | 24 | 3l | 50 |
13 | Thiophene-2-yl | 4-ClC6H4 | 12 | 3m | 62 |
14 | 3,4-Cl2C6H3 | 4-CH3CH2C6H4 | 12 | 3n | 70 |
15 | 4-CH3OC6H4 | 4-CH3CH2C6H4 | 24 | 3o | 45 |
16 | Thiophene-2-yl | 4-CH3CH2C6H4 | 12 | 3p | 60 |
Entry | R | Ar | Time/h | Product | Yield/% |
---|---|---|---|---|---|
1 | 4-ClC6H4 | C6H5 | 12 | 3a | 70 |
2 | 4-BrC6H4 | C6H5 | 12 | 3b | 68 |
3 | 4-FC6H4 | C6H5 | 12 | 3c | 58 |
4 | 3-BrC6H4 | C6H5 | 12 | 3d | 65 |
5 | 3,4-Cl2C6H3 | C6H5 | 12 | 3e | 75 |
6 | 4-O2NC6H4 | C6H5 | 12 | 3f | 74 |
7 | 4-CH3OC6H4 | C6H5 | 24 | 3g | 48 |
8 | Thiophene-2-yl | C6H5 | 12 | 3h | 58 |
9 | 3,4-Cl2C6H3 | 4-ClC6H4 | 12 | 3i | 73 |
10 | 4-ClC6H4 | 4-ClC6H4 | 12 | 3j | 68 |
11 | 4-NO2C6H4 | 4-ClC6H4 | 12 | 3k | 76 |
12 | 4-CH3OC6H4 | 4-ClC6H4 | 24 | 3l | 50 |
13 | Thiophene-2-yl | 4-ClC6H4 | 12 | 3m | 62 |
14 | 3,4-Cl2C6H3 | 4-CH3CH2C6H4 | 12 | 3n | 70 |
15 | 4-CH3OC6H4 | 4-CH3CH2C6H4 | 24 | 3o | 45 |
16 | Thiophene-2-yl | 4-CH3CH2C6H4 | 12 | 3p | 60 |
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