[2] 📄 (E)-Selective Friedel–Crafts acylation of alkynes to β-chlorovinyl ketones: defying isomerizations in batch reactions by flow chemistry approaches
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요약 정보
| 출판일 | 2019.04.11 |
| 출판사 | Royal Society of Chemistry |
| 저자 | Hyungmo Koo |
| DOI | https://doi.org/10.1039/C9QO00217K |
| 구매링크 | https://pubs.rsc.org/en/content/articlelanding/2019/QO/C9QO00217K#!divAbstract |
저널 정보
TOC
Abstract
The Friedel–Crafts acylation of alkynes stereoselectively provides (Z)-β-chlorovinyl ketones, whereas the AlCl3-promoted reaction yields a mixture of stereoisomeric β-chlorovinyl ketones. To develop the (E)-selective synthesis of β-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)-β-chlorovinyl ketones.
Citation
Org. Chem. Front., 2019, 6, 1868-1872
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