化学
烯丙基重排
亲核细胞
电泳剂
碳负离子
取代反应
试剂
反应性(心理学)
有机化学
亲核取代
组合化学
烷基
正在离开组
药物化学
催化作用
替代医学
病理
医学
作者
Artem A. Zemtsov,Vitalij V. Levin,Alexander D. Dilman
标识
DOI:10.1016/j.ccr.2022.214455
摘要
The importance of organofluorine compounds has spurred the development of methods aimed at their synthesis. In this review, carbon–carbon bond forming reactions between allylic electrophiles and fluorinated nucleophiles are discussed. Compared to classical saturated alkyl halides, allylic electrophiles have increased reactivity especially in transition metal mediated processes, which is associated with propensity of the allylic systems to interact with low-valent transition metal complexes. Due to specific electronic effects, fluorine atoms may have a profound impact on the stability and reactivity of carbanionic reagents. In the review, nucleophilic reagents bearing one, two or three fluorine atoms at the nucleophilic carbon are considered. Various types of fluorinated reagents including silicon, copper, and zinc derivatives, employed both in catalytic or stoichiometric variants, as well as reagents having a stabilized fluorinated carbanion, are presented. The review is comprehensive, and covers the literature starting from the earlier work on conventional nucleophilic substitution reactions up to recent transition metal catalyzed processes.
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