Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 17, Issue 9, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202200184
Keywords
anti-Markovnikov Addition; Iodofluorination; Alkenes; Fluorine; Tertiary C-F bonds
Categories
Funding
- National Key Research and Development Program of China [2021YFF0701700]
- National Natural Science Foundation [21971252, 21991122, 21672138]
- Key Research Program of Frontier Sciences, Chinese Academy of Sciences (CAS) [QYZDJSSWSLH049]
- Science and Technology Commission of Shanghai Municipality [22ZR1423600]
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In this paper, a convenient anti-Markovnikov iodofluorination of alkenes was described using Selectfluor/(Bu4NI)-Bu-n as the reagent. The reaction showed a broad substrate scope, good functional group tolerance, and the ability to construct various C-F bonds.
The fluorination of alkenes with electrophilic N-F type reagents usually occurs through a Markovnikov-type addition, and the anti-Markovnikov-type addition may require the use of a transition metal catalyst or an expensive catalyst. Herein we describe a convenient anti-Markovnikov iodofluorination of alkenes with Selectfluor/(Bu4NI)-Bu-n. A wide substrate scope and good functional group tolerance were observed. The process allows for the construction of various C-F bonds, especially tertiary C-F bonds. The remarkable features make this protocol attractive, including convenient operations, simple reaction conditions, and the installation of an iodine atom which provides possibilities for further transformations.
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