期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 14, 页码 3825-3829出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712725
关键词
aromaticity; bismuth; CH activation; cationic species; density functional calculations
资金
- Netherlands Organization for Scientific Research (NWO)
- Fonds der Chemischen Industrie
- Spanish MINECO [CTQ2016-77558-R]
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.
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