Amidocuprates for directed ortho cupration: Structural study, mechanistic investigation, and chemical requirements

Shinsuke Komagawa, Shinya Usui, Joanna Haywood, Philip J. Harford, Andrew E.H. Wheatley, Yotaro Matsumoto, Keiichi Hirano, Ryo Takita, Masanobu Uchiyama

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The name of the game: X-ray crystallographic analysis of Gilman- and Lipshutz-type amidocuprates indicates that the presence of LiX (X=CN, I) and THF shifts the equilibrium between the two toward the Lipshutz-type cuprate and that this is important in generating the active species for directed ortho cupration. DFT calculations show that monomeric Gilman-type cuprates have an unprecedentedly high reactivity (see scheme, DG=directing group).

Original languageEnglish
Pages (from-to)12081-12085
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number48
DOIs
Publication statusPublished - 2012 Nov 26

Keywords

  • cuprates
  • density functional calculations
  • mechanistic studies
  • ortho metalation
  • structure elucidation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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