Enolonium Species-Umpoled Enolates

Research output: Contribution to journalJournal article – Annual report year: 2017Researchpeer-review

DOI

  • Author: Arava, Shlomy

    Ariel University Center of Samaria, Israel

  • Author: Kumar, Jayprakash N.

    Ariel University Center of Samaria, Israel

  • Author: Maksymenko, Shimon

    Ariel University Center of Samaria, Israel

  • Author: Iron, Mark A.

    Weizmann Institute of Science, Israel

  • Author: Parida, Keshaba N.

    Ariel University Center of Samaria, Israel

  • Author: Fristrup, Peter

    Department of Chemistry, Technical University of Denmark

  • Author: Szpilman, Alex M.

    Ariel University Center of Samaria, Israel

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Enolonium species/iodo(III) enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C-O, α-C-N, α-C-C, and alpha-carbon- halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at-78 degrees C, and report the first spectroscopic identification of such species. It is shown that enolonium species are direct intermediates in C-O, C-N, C-Cl, and C-C bond forming reactions. Our results open up chemical space for designing a variety of new transformations. We showcase the ability of enolonium species to react with prenyl, crotyl, cinnamyl, and allyl silanes with absolute regioselectivity in up to 92% yield.
Original languageEnglish
JournalAngewandte chemie-international edition
Volume56
Pages (from-to)2599-2603
ISSN1433-7851
DOIs
Publication statusPublished - 2017
CitationsWeb of Science® Times Cited: No match on DOI

    Research areas

  • allylation, enolonium species , ketones, polarity inversion , umpolung

ID: 130801978