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Unveiling Hetero‐Enyne Reactivity of Aryliminoboranes: Dearomative Hetero‐Diels–Alder‐Like Reactions.
- Source :
- Angewandte Chemie International Edition; 8/22/2022, Vol. 61 Issue 34, p1-6, 6p
- Publication Year :
- 2022
-
Abstract
- Being isoelectronic with alkynes, iminoboranes with a polar B≡N triple bond have been exclusively investigated as a potent 1,2‐dipole in synthetic chemistry. Herein, we disclose the unprecedented reactivity of aryliminoboranes via the BNCC π conjugation, namely hetero‐enyne behavior. This allows for facile dearomative Diels–Alder‐like reactions of aryliminoboranes with aldehydes. This cycloaddition features mild conditions, is catalyst‐free, and has a broad substrate scope and good functional group tolerance. Kinetic and computational studies reveal its second‐order reaction and concerted cyclization mechanism. This report unveils new synthetic application of iminoboranes beyond their classical reaction patterns. [ABSTRACT FROM AUTHOR]
- Subjects :
- FUNCTIONAL groups
ALDEHYDES
RING formation (Chemistry)
ALKYNES
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 61
- Issue :
- 34
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 158571900
- Full Text :
- https://doi.org/10.1002/anie.202205814