Bronsted Acid Catalyzed Oxygenative Bimolecular Friedel-Crafts-type Coupling of Ynamides
- Authors
- Patil, Dilip V.; Kim, Seung Woo; Nguyen, Quynh H.; Kim, Hanbyul; Wang, Shan; Hoang, Tuan; Shin, Seunghoon
- Issue Date
- Mar-2017
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- Bronsted acid catalysis; intermolecular trapping; pyridine-N-oxides; ynamides; alpha-oxo carbene surrogate
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.56, no.13, pp.3670 - 3674
- Indexed
- SCIE
SCOPUS
- Journal Title
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Volume
- 56
- Number
- 13
- Start Page
- 3670
- End Page
- 3674
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/152835
- DOI
- 10.1002/anie.201612471
- ISSN
- 1433-7851
- 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.
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