Journal
ORGANIC LETTERS
Volume 21, Issue 17, Pages 6893-6896Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02516
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Funding
- National Natural Science Foundation of China [21472068]
- MOE&SAFEA for the 111 Project [B13025]
- national first-class discipline program of Food Science and Technology [JUFSTR20180204]
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We report herein a strategy of ammonium hydrogen-bonding-assisted alpha-F elimination from Cu-CF3 compounds that generates R3N center dot HF reagents in situ. Combining this strategy and Cu(III)-CF3 chemistry with alkynes, dual fluorination and trifluoromethylation of terminal alkynes is enabled by a single Cu(III)-CF3 compound assisted by a tertiary amine with excellent regio-and stereoselectivity. This strategy also enables the development of other reaction types involving trapping of the in situ-formed R3N center dot HF reagents by other electrophilic groups and can be used for the late-stage functionalization of estrone derivatives.
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