(E)-Selective Friedel-Crafts acylation of alkynes to beta-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches
- Authors
- Koo, Hyungmo; Kim, Hun Young; Oh, Kyungsoo
- Issue Date
- Jun-2019
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC CHEMISTRY FRONTIERS, v.6, no.11, pp 1868 - 1872
- Pages
- 5
- Journal Title
- ORGANIC CHEMISTRY FRONTIERS
- Volume
- 6
- Number
- 11
- Start Page
- 1868
- End Page
- 1872
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/32724
- DOI
- 10.1039/c9qo00217k
- ISSN
- 2052-4129
2052-4129
- Abstract
- The Friedel-Crafts acylation of alkynes stereoselectively provides (Z)-beta-chlorovinyl ketones, whereas the AlCl3-promoted reaction yields a mixture of stereoisomeric beta-chlorovinyl ketones. To develop the (E)-selective synthesis of beta-chlorovinyl ketones, a flow chemistry approach was devised for the Friedel-Crafts acylation of alkynes that defies the facile (E). (Z) isomerization under the AlCl3-promoted reaction conditions. Compared to batch reactions, the flow chemistry approach provides a fast, clean, high yielding, and stereoselective synthetic route to (E)-beta-chlorovinyl ketones.
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Collections - College of Pharmacy > School of Pharmacy > 1. Journal Articles
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