Copper Catalyzed Three-Component Ullmann C-S Coupling in PEG for the Synthesis of 6-Aryl/alkylthio-purines
To tackle the environmental unfriendly issue in existing synthesis strategies for 6-substitued thiopurine derivatives, such as poor step economy, frequent use of malodorous organic sulfur starting materials, toxic organic solvents, and equivalent dosage of base, we have developed a CuI-catalyzed base-free three-component Ullmann C-S coupling synthetic strategy, featured using inorganic salt Na2S as the sulfur source and nontoxic PEG-600 as the solvent. The newly developed strategy is particularly effective for the synthesis of 6-arylthiopurines. The high catalytic efficiency in PEG-600 can be rationalized by the high soluble ability of CuI catalyst, likely due to the presence of multiple oxygen coordination sites in PEG.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:89 |
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| Enthalten in: |
The Journal of organic chemistry - 89(2024), 4 vom: 16. Feb., Seite 2212-2222 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Panpan [VerfasserIn] |
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| Links: |
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| Themen: |
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| Anmerkungen: |
Date Revised 16.02.2024 published: Print-Electronic Citation Status PubMed-not-MEDLINE |
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| doi: |
10.1021/acs.joc.3c02116 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM368010481 |
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| 500 | |a Date Revised 16.02.2024 | ||
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| 500 | |a Citation Status PubMed-not-MEDLINE | ||
| 520 | |a To tackle the environmental unfriendly issue in existing synthesis strategies for 6-substitued thiopurine derivatives, such as poor step economy, frequent use of malodorous organic sulfur starting materials, toxic organic solvents, and equivalent dosage of base, we have developed a CuI-catalyzed base-free three-component Ullmann C-S coupling synthetic strategy, featured using inorganic salt Na2S as the sulfur source and nontoxic PEG-600 as the solvent. The newly developed strategy is particularly effective for the synthesis of 6-arylthiopurines. The high catalytic efficiency in PEG-600 can be rationalized by the high soluble ability of CuI catalyst, likely due to the presence of multiple oxygen coordination sites in PEG | ||
| 650 | 4 | |a Journal Article | |
| 700 | 1 | |a Liu, Yunfang |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Xulian |e verfasserin |4 aut | |
| 700 | 1 | |a Siri, Geling |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Jieyuan |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Zhen |e verfasserin |4 aut | |
| 700 | 1 | |a Jian, Yajun |e verfasserin |4 aut | |
| 700 | 1 | |a Gao, Ziwei |e verfasserin |4 aut | |
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