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

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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

Funding

C.L. thanks Dr. Rian Dewhurst for helpful discussions and Prof. Holger Braunschweig for his continuous support. Funding by the Fonds der Chemischen Industrie (Liebig fellowship to C.L.), the Netherlands Organization for Scientific Research (NWO), and the Spanish MINECO (CTQ2016-77558-R) is acknowledged.

FundersFunder number
Netherlands Organization for Scientific Research
Verband der Chemischen Industrie
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Ministerio de Economía y CompetitividadCTQ2016-77558-R

    Keywords

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

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