Abstract: 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.

Cite: Zemtsov A.A. , Levin V.V. , Dilman A.D.
Allylic substitution reactions with fluorinated nucleophiles
Coordination Chemistry Reviews. 2022. V.459. 214455 . DOI: 10.1016/j.ccr.2022.214455 WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:000788731400003
Scopus:	2-s2.0-85124586923
OpenAlex:	W4212864361

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