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 bas...
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| Veröffentlicht in: | Journal of organic chemistry 2024-02, Vol.89 (4), p.2212-2222 |
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| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Zhang, Panpan Liu, Yunfang Li, Xulian Siri, Geling Wang, Jieyuan Li, Zhen Jian, Yajun Gao, Ziwei |
| description | 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. |
| doi_str_mv | 10.1021/acs.joc.3c02116 |
| format | Article |
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The newly developed strategy is particularly effective for the synthesis of 6-arylthiopurines. 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Org. Chem</addtitle><date>2024-02-16</date><risdate>2024</risdate><volume>89</volume><issue>4</issue><spage>2212</spage><epage>2222</epage><pages>2212-2222</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>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. 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| source | ACS Publications |
| title | Copper Catalyzed Three-Component Ullmann C–S Coupling in PEG for the Synthesis of 6‑Aryl/alkylthio-purines |
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