Zinc-Mediated C-H Metalations in Modern Organic Synthesis

Daria K. Wanic, Rebecca Melvin, Graeme Barker

Research output: Contribution to journalArticlepeer-review

Abstract

C-H deprotometalations have long occupied a key role in modern organic synthesis in both the research laboratory and pharmaceutical and fine chemical manufacture, thanks to readily accessible reagents and well-established procedures. Typically, organolithiums are the reagent of choice thanks to high reactivity and ease of use but these are incompatible with base- and nucleophile-sensitive functional groups. In comparison, organozinc base complexes offer a milder approach to deprotonative C-H functionalisations, and compatibility with a wide range of functionalities which would be problematic when using the alternative organolithium or organomagnesium reagents has now been demonstrated. Here, we review the current state of the art in zinc-mediated C-H metalations at substituted arenes, heteroarenes and Csp3-H sites.
Original languageEnglish
Pages (from-to)3487-3501
Number of pages15
JournalSynthesis
Volume55
Issue number21
Early online date15 Sept 2023
DOIs
Publication statusPublished - Nov 2023

Keywords

  • C-H Functionalisation
  • Deprotonation
  • Metalation
  • Organozinc

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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