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Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins with alcohols
Liu, Zhuqing1,2; Huang, Fei1,2; Lou, Jiang1,2; Wang, Quannan1,2; Yu, Zhengkun1
Source PublicationORGANIC & BIOMOLECULAR CHEMISTRY
2017-07-14
DOI10.1039/c7ob01234a
Volume15Pages:5535-5540
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordO BOND FORMATION ; OXO KETENE DITHIOACETALS ; ARYL ETHERS ; UNACTIVATED C(SP(3))-H ; EFFICIENT SYNTHESIS ; CATALYZED ETHERIFICATION ; C(SP(2))-H BONDS ; ENOL ETHERS ; FUNCTIONALIZATION ; ACTIVATION
AbstractCopper-promoted direct C-H alkoxylation of S, S-functionalized internal olefins, that is, alpha-oxo ketene dithioacetals, was efficiently achieved with alcohols as the alkoxylating agents, (diacetoxyiodo)benzene (PhI(OAc)(2)) as the oxidant, and benzoquinone (BQ) as the co-oxidant. The alkoxylated olefins were thus constructed and applied for the synthesis of alkoxylated N-heterocycles. The polarization of the olefinic carbon-carbon double bond by the electron-donating dialkylthio and electron-withdrawing alpha-oxo functionalities plays a crucial role in making such C-H alkoxylation reactions to occur under mild conditions. Mechanistic studies implicate a single-electron-transfer (SET) reaction pathway involved in the overall catalytic cycle.
Language英语
WOS IDWOS:000405003900012
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Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/152068
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Liaoning, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Liu, Zhuqing,Huang, Fei,Lou, Jiang,et al. Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins with alcohols[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2017,15:5535-5540.
APA Liu, Zhuqing,Huang, Fei,Lou, Jiang,Wang, Quannan,&Yu, Zhengkun.(2017).Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins with alcohols.ORGANIC & BIOMOLECULAR CHEMISTRY,15,5535-5540.
MLA Liu, Zhuqing,et al."Copper-promoted direct C-H alkoxylation of S,S-functionalized internal olefins with alcohols".ORGANIC & BIOMOLECULAR CHEMISTRY 15(2017):5535-5540.
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