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

Research output: Contribution to journalArticle (Academic Journal)

5 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)3917-3921
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number10
Early online date8 Jan 2020
DOIs
Publication statusPublished - 2 Mar 2020

Keywords

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

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