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Title: Electrophilic Activation of Iodonium Ylides by Halogen-Bond-Donor Catalysis for Cross-Enolate Coupling
Authors: Saito, Masato
Kobayashi, Yusuke
Tsuzuki, Seiji
Takemoto, Yoshiji
Author's alias: 斎藤, 真人
小林, 祐輔
竹本, 佳司
Keywords: organocatalyst
umpolung
hypervalent iodine
XB donor
Issue Date: 19-Jun-2017
Publisher: Wiley
Journal title: Angewandte Chemie International Edition
Volume: 56
Issue: 26
Start page: 7653
End page: 7657
Abstract: The umpolung alkylation of silyl enol ethers with an iodonium(III) ylide proceeds under mild conditions to afford various 1, 4‐dicarbonyl compounds in high yields in the presence of a halogen‐bonding catalyst. Unlike typical transition‐metal activation processes of such ylide precursors, which tend to proceed via carbenoid intermediates, experimental and computational studies indicate that halogen bonding (XB) between the XB donor catalyst and the iodonium ylide plays a crucial role in promoting the reaction. The identification of a compatible Bronsted base catalyst enabled the extension of this method to enols generated in situ to give the corresponding adducts in good yields.
Rights: This is the peer reviewed version of the following article: [Masato Saito, Yusuke Kobayashi, Seiji Tsuzuki, Yoshiji Takemoto. Electrophilic Activation of Iodonium Ylides by Halogen‐Bond‐Donor Catalysis for Cross‐Enolate Coupling. Angewandte Chemie International Edition, 56(26), 7653-7657], which has been published in final form at https://doi.org/10.1002/anie.201703641. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
The full-text file will be made open to the public on 09 June 2018 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/243149
DOI(Published Version): 10.1002/anie.201703641
PubMed ID: 28500729
Appears in Collections:Journal Articles

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