1. Cross‐ and Multi‐Coupling Reactions Using Monofluoroalkanes.
- Author
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Iwasaki, Takanori and Kambe, Nobuaki
- Subjects
- *
SCISSION (Chemistry) , *ORGANIC synthesis , *LEWIS acids , *CHARGE exchange , *FRIEDEL-Crafts reaction - Abstract
Carbon‐fluorine bonds are stable and have demonstrated sluggishness against various chemical manipulations. However, selective transformations of C−F bonds can be achieved by developing appropriate conditions as useful synthetic methods in organic chemistry. This review focuses on C−C bond formation at monofluorinated sp3‐hybridized carbons via C−F bond cleavage, including cross‐coupling and multi‐component coupling reactions. The C−F bond cleavage mechanisms on the sp3‐hybridized carbon centers can be primarily categorized into three types: Lewis acids promoted F atom elimination to generate carbocation intermediates; nucleophilic substitution with metal or carbon nucleophiles supported by the activation of C−F bonds by coordination of Lewis acids; and the cleavage of C−F bonds via a single electron transfer. The characteristic features of alkyl fluorides, in comparison with other (pseudo)halides as promising electrophilic coupling counterparts, are also discussed. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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