Journal
ORGANIC LETTERS
Volume 23, Issue 15, Pages 6062-6066Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02139
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Funding
- National Natural Science Foundation of China [21772142, 21901181, 21961142015]
- National Key Research and Development Program of China [2019YFA0905100]
- Tianjin Municipal Science & Technology Commission [19JCQNJC04700]
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An unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines promoted by diethylzinc is described, which involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, providing a broad array of 3-trifluoromethyl pyrazolines in good yields with excellent diastereoselectivities. Further transformations allow for facile access to 3-trifluoromethyl pyrazoles and 3,5-ditrifluoromethyl pyridazines with good efficiency.
A diethylzinc-promoted unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines is described. This transformation involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, thus giving a broad array of 3-trifluoromethyl pyrazolines in good yields with excellent diastereoselectivities. Further transformations provide facile access to 3-trifluoromethyl pyrazoles and 3,5-ditrifluoromethyl pyridazines with good efficiency.
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