Double CH Activation of a Masked Cationic Bismuth Amide

Benedikt Ritschel, Jordi Poater, Hannah Dengel, F. Matthias Bickelhaupt*, Crispin Lichtenberg

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The transformation of C−H bonds into more reactive C−M bonds amenable to further functionalization is of fundamental importance in synthetic chemistry. We demonstrate here that the transformation of neutral bismuth compounds into their cationic analogues can be used as a strategy to facilitate CH activation reactions. In particular, the double CH activation of bismuth-bound diphenyl amide, (NPh2), is reported along with simple one-pot procedures for the functionalization of the activated positions. The organometallic products of the first and second CH activation steps were isolated in high yields. Analysis by NMR spectroscopy, single-crystal X-ray diffraction, and DFT calculations revealed unusual ground-state properties (e.g., ring strain, moderate heteroaromaticity), and provided mechanistic insight into the formation of these compounds.

Original languageEnglish
Pages (from-to)3825-3829
Number of pages5
JournalAngewandte Chemie. International Edition
Volume57
Issue number14
Early online date1 Feb 2018
DOIs
Publication statusPublished - 26 Mar 2018

Keywords

  • aromaticity
  • bismuth
  • cationic species
  • CH activation
  • density functional calculations

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