期刊
JOURNAL OF FLOW CHEMISTRY
卷 10, 期 1, 页码 139-143出版社
SPRINGER
DOI: 10.1007/s41981-019-00057-6
关键词
Fritsch-Buttemberg-Wiechell rearrangement; Carbenoid; Organolithium compounds; Selectivity; Microfluidics
资金
- European France-(Manche)-England cross-border cooperation program INTERREG IV A AI-CHEM CHANNEL
- European France-(Manche)-England cross-border cooperation program INTERREG V A LABFACT
- ERDF
- Labex SYNORG [ANR-11-LABX-0029]
- Ministerio de Educacion Superior, Ciencia y Tecnologia of the Dominican Republic
The generation and reactivity of two model vinyl carbenoids from gem-dibromoalkenes 1 were studied in microflow systems. From substrate 1a (R = Ph, CF3), the lithium-bromine exchange could be simply performed within 30 ms at 20 degrees C with very good E-selectivity whereas the reaction was unselective under batch conditions, even at -78 degrees C. Moreover, the unstable carbenoid generated from 1b (R = Ph, H) could be trapped as the major product while only the Fritsch-Buttemberg-Wiechell rearrangement product was obtained in a flask under cryogenic conditions.
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