Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1691-1702.DOI: 10.6023/cjoc202010023 Previous Articles Next Articles
ARTICLES
收稿日期:
2020-10-16
修回日期:
2020-11-11
发布日期:
2020-12-05
通讯作者:
程凯, 黄乐浩
基金资助:
Honglei Jina, Fengxuan Jiangb, Kai Chengb,*(), Lehao Huanga,*()
Received:
2020-10-16
Revised:
2020-11-11
Published:
2020-12-05
Contact:
Kai Cheng, Lehao Huang
About author:
Supported by:
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Honglei Jin, Fengxuan Jiang, Kai Cheng, Lehao Huang. Palladium-Catalyzed C8 Alkylation of 1-Naphthylamides and Its Application to the Synthesis of the Core Sturctures of Aporphine and Aristolactam Alkaloids[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1691-1702.
Entry | Catalyst/mol% | Additive | Solvent | Yieldb/% |
---|---|---|---|---|
1 | Pd(OAc)2 | KOAc | 1,4-Dioxane | 61 |
2 | Pd(OAc)2 | PhCOOK | 1,4-Dioxane | 68 |
3 | Pd(OAc)2 | PhCOOK | DMF | N.D. |
4 | Pd(OAc)2 | PhCOOK | Xylene | 82 |
5 | Pd(OAc)2 | PhCOOK | DMSO | N.D. |
6 | Pd(OAc)2 | PhCOOK | t-BuOH | 75 |
7 | Pd(OAc)2 | PhCOOK | DCE | 86 |
8 | Pd(OAc)2 | — | DCE | Trace |
9 | Pd(OAc)2 | AgOAc | DCE | Trace |
10 | Pd(OAc)2 | NaOAc | DCE | 49 |
11 | Pd(OAc)2 | K2CO3 | DCE | 45 |
12 | Pd(OAc)2 | Cs2CO3 | DCE | Trace |
13 | Pd(OAc)2 | HOAc | DCE | 18 |
14 | Pd(OAc)2 | CF3COOH | DCE | N.D. |
15 | PdCl2 | PhCOOK | DCE | 83 |
16 | Pd(PPh3)4 | PhCOOK | DCE | 36 |
17 | Pd2(dba)3 | PhCOOK | DCE | 30 |
18 | Pd(CH3CN)2Cl2 | PhCOOK | DCE | 80 |
Entry | Catalyst/mol% | Additive | Solvent | Yieldb/% |
---|---|---|---|---|
1 | Pd(OAc)2 | KOAc | 1,4-Dioxane | 61 |
2 | Pd(OAc)2 | PhCOOK | 1,4-Dioxane | 68 |
3 | Pd(OAc)2 | PhCOOK | DMF | N.D. |
4 | Pd(OAc)2 | PhCOOK | Xylene | 82 |
5 | Pd(OAc)2 | PhCOOK | DMSO | N.D. |
6 | Pd(OAc)2 | PhCOOK | t-BuOH | 75 |
7 | Pd(OAc)2 | PhCOOK | DCE | 86 |
8 | Pd(OAc)2 | — | DCE | Trace |
9 | Pd(OAc)2 | AgOAc | DCE | Trace |
10 | Pd(OAc)2 | NaOAc | DCE | 49 |
11 | Pd(OAc)2 | K2CO3 | DCE | 45 |
12 | Pd(OAc)2 | Cs2CO3 | DCE | Trace |
13 | Pd(OAc)2 | HOAc | DCE | 18 |
14 | Pd(OAc)2 | CF3COOH | DCE | N.D. |
15 | PdCl2 | PhCOOK | DCE | 83 |
16 | Pd(PPh3)4 | PhCOOK | DCE | 36 |
17 | Pd2(dba)3 | PhCOOK | DCE | 30 |
18 | Pd(CH3CN)2Cl2 | PhCOOK | DCE | 80 |
Entry | α-Bromo ketones | Product | Yieldb/% | Entry | α-Bromo ketones | Product | Yieldb/% |
---|---|---|---|---|---|---|---|
1 | | 3f | 82 (74c) | 6 | | 3k | 70 |
2 | | 3g | 79 | 7 | | 3l | 78 |
3 | | 3h | 64 | 8 | | 3m | 71 |
4 | | 3i | 55 | 9 | | 3n | 52 |
5 | | 3j | 76 | 10d | | 3o | 56 |
Entry | α-Bromo ketones | Product | Yieldb/% | Entry | α-Bromo ketones | Product | Yieldb/% |
---|---|---|---|---|---|---|---|
1 | | 3f | 82 (74c) | 6 | | 3k | 70 |
2 | | 3g | 79 | 7 | | 3l | 78 |
3 | | 3h | 64 | 8 | | 3m | 71 |
4 | | 3i | 55 | 9 | | 3n | 52 |
5 | | 3j | 76 | 10d | | 3o | 56 |
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