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Copper-promoted direct C–H alkoxylation of S,S-functionalized internal olefins with alcohols

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Abstract

Copper-promoted direct C–H alkoxylation of S,S-functionalized internal olefins, that is, α-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 α-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.

Graphical abstract: Copper-promoted direct C–H alkoxylation of S,S-functionalized internal olefins with alcohols

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Publication details

The article was received on 19 May 2017, accepted on 13 Jun 2017 and first published on 13 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01234A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Copper-promoted direct C–H alkoxylation of S,S-functionalized internal olefins with alcohols

    Z. Liu, F. Huang, J. Lou, Q. Wang and Z. Yu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01234A

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