Bronsted Acid Catalyzed Oxygenative Bimolecular Friedel-Crafts-type Coupling of Ynamides
- Title
- Bronsted Acid Catalyzed Oxygenative Bimolecular Friedel-Crafts-type Coupling of Ynamides
- Author
- 신승훈
- Keywords
- Bronsted acid catalysis; intermolecular trapping; pyridine-N-oxides; ynamides; alpha-oxo carbene surrogate
- Issue Date
- 2017-02
- Publisher
- WILEY-V C H VERLAG GMBH
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 56, no. 13, page. 3670-3674
- Abstract
- A non-metal approach for accessing alpha-oxo carbene surrogates for a C-C bond-forming bimolecular coupling between ynamides and nucleophilic arenes was developed. This acid-catalyzed coupling features mild temperature, which is critical for the required temporal chemoselectivity among nucleophiles. The scope of nucleophiles includes indoles, pyrroles, anilines, phenols and silyl enolethers. Furthermore, a direct test of S(N)2' mechanism has been provided by employing chiral N,N'-dioxides which also enlightens the nature of the intermediates in related metal-catalyzed processes.
- URI
- https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201612471https://repository.hanyang.ac.kr/handle/20.500.11754/112683
- ISSN
- 1433-7851; 1521-3773
- DOI
- 10.1002/anie.201612471
- Appears in Collections:
- COLLEGE OF NATURAL SCIENCES[S](자연과학대학) > CHEMISTRY(화학과) > Articles
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