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1,3-Difunctionalizations of [1.1.1]Propellane via 1,2-Metallate Rearrangements of Boronate Complexes

Research output: Contribution to journalArticle

Original languageEnglish
Number of pages6
JournalAngewandte Chemie - International Edition
Early online date8 Jan 2020
DOIs
DateAccepted/In press - 21 Nov 2019
DateE-pub ahead of print - 8 Jan 2020
DatePublished (current) - 28 Jan 2020

Abstract

1,3‐Disubstituted bicyclo[1.1.1]pentanes (BCPs) are valuable bioisosteres of para ‐substituted aromatic rings. The most direct route to these structures is via multi‐component ring‐opening reactions of [1.1.1]propellane. However, challenges associated with these transformations mean that difunctionalized BCPs are more commonly prepared via multistep reaction sequences with BCP‐halide intermediates. Herein, we report three‐ and four‐component 1,3‐difunctionalizations of [1.1.1]propellane with organometallic reagents, organoboronic esters and a variety of electrophiles. This is achieved by trapping intermediate BCP‐metal species with boronic esters to form boronate complexes, which are versatile intermediates whose electrophile‐induced 1,2‐metallate rearrangement chemistry enables a broad range of C–C bond‐forming reactions.

    Research areas

  • [1.1.1]Propellan, Bicyclo[1.1.1]pentane, Borylierung, Mehrkomponentenreaktionen, Zweifel-Olefinierung

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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/full/10.1002/ange.201914875 . Please refer to any applicable terms of use of the publisher.

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