碳阳离子
化学
电泳剂
亲核细胞
键裂
劈理(地质)
卤化物
偶联反应
路易斯酸
烷基
氟
亲核取代
组合化学
光化学
计算化学
药物化学
有机化学
催化作用
岩土工程
断裂(地质)
工程类
作者
Takanori Iwasaki,Nobuaki Kambe
标识
DOI:10.1002/tcr.202300033
摘要
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.
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