期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 363, 期 14, 页码 3600-3606出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202100441
关键词
C-H functionalization; Rodium; Heterocycles; Alkynes; Fluorine
资金
- National Natural Science Foundation of China [U2004189]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [20IRTSTHN005]
- Natural Science Foundation of Henan Province [212300410364]
- Henan Key Laboratory of Organic Functional Molecules and Drug Innovation
- 111 Project [D17007]
This study presents a selective synthesis of 3-(alpha-fluorovinyl)indoles and 3-acylindoles via a cascade process, demonstrating potential as lead compounds for drug development with controllable selectivity and simultaneous formation of diverse compounds.
Presented herein is a selective synthesis of 3-(alpha-fluorovinyl)indoles and 3-acylindoles via the coupling of 1-phenylpyrazolidinones with alpha,alpha-difluoromethylene alkynes. Mechanistically, the formation of 3-(alpha-fluorovinyl)indoles is resulted from a cascade process including Rh(III)-catalyzed ortho-C-H bond cleavage, regioselective triple bond insertion, pyrazolidinone ring-opening, indole ring-formation and HF elimination. Interestingly, when this reaction was carried out in CH3OH/H2O instead of CH3CN, the in situ formed 3-(alpha-fluorovinyl)indoles readily undergo a hydration process to afford 3-acylindole derivatives. This protocol features with controllable selectivity, simultaneous formation of both the heterocyclic scaffold and the monofluoroalkenyl moiety, atom-economy, substrate diversity, good functional group tolerance and redox-neutral reaction conditions. Anticancer screening of selected products against two human cancer cell lines demonstrated their potential as lead compounds for drug development.
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