{"title":"水介质中 VOSO4 与 Cu(0) 结合催化的便捷叠氮-炔 Huisgen 环加成反应","authors":"Wen-Chieh Yang, and , Chien-Tien Chen*, ","doi":"10.1021/acsorginorgau.3c00059","DOIUrl":null,"url":null,"abstract":"<p >A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl β-azido glycosides with three different terminal alkynes in CH<sub>3</sub>CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.</p>","PeriodicalId":29797,"journal":{"name":"ACS Organic & Inorganic Au","volume":"4 2","pages":"235–240"},"PeriodicalIF":3.3000,"publicationDate":"2023-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00059","citationCount":"0","resultStr":"{\"title\":\"Expedient Azide–Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO4 with Cu(0) in Aqueous Media\",\"authors\":\"Wen-Chieh Yang, and , Chien-Tien Chen*, \",\"doi\":\"10.1021/acsorginorgau.3c00059\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl β-azido glycosides with three different terminal alkynes in CH<sub>3</sub>CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.</p>\",\"PeriodicalId\":29797,\"journal\":{\"name\":\"ACS Organic & Inorganic Au\",\"volume\":\"4 2\",\"pages\":\"235–240\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2023-12-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://pubs.acs.org/doi/epdf/10.1021/acsorginorgau.3c00059\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Organic & Inorganic Au\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00059\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Organic & Inorganic Au","FirstCategoryId":"1085","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acsorginorgau.3c00059","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Expedient Azide–Alkyne Huisgen Cycloaddition Catalyzed by a Combination of VOSO4 with Cu(0) in Aqueous Media
A series of vanadium(III), vanadyl(IV/V) species, inorganic metal oxides, and transition-metal oxides was examined as cocatalysts with Cu(0) powder for copper(I)-catalyzed azide-alkyne cycloaddition. Among them, vanadyl(IV) species bearing acetylacetonate, acetate, and sulfate, vanadyl(V) isopropoxide, and vanadate were suitable for the click reactions of per-acetyl and per-benzyl β-azido glycosides with three different terminal alkynes in CH3CN. Water-soluble vanadyl(IV) sulfate was further selected for efficient click reactions for unprotected β-glycosyl azides and even compatible with a thiol-containing substrate in aqueous media at ambient temperature.
期刊介绍：
ACS Organic & Inorganic Au is an open access journal that publishes original experimental and theoretical/computational studies on organic organometallic inorganic crystal growth and engineering and organic process chemistry. Short letters comprehensive articles reviews and perspectives are welcome on topics that include:Organic chemistry Organometallic chemistry Inorganic Chemistry and Organic Process Chemistry.
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