Nickel-Catalyzed Alkylcarbonylation of α-Trifluoromethyl Substituted Styrenes via Selective Monodefluorinative Strategy

Donghao Luo; Hao Yuan; Changrui Nie; Shulei Ge; Jie Li

doi:10.1055/a-2617-6013

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Synthesis
DOI: 10.1055/a-2617-6013

paper

Nickel-Catalyzed Alkylcarbonylation of α-Trifluoromethyl Substituted Styrenes via Selective Monodefluorinative Strategy

Donghao Luo

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)

,

Hao Yuan

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)

,

Changrui Nie

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)

,

Shulei Ge

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)

,

Jie Li

¹College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)

› InstitutsangabenGefördert durch: Jiangsu Specially Appointed Professors Plan SR10900122
Gefördert durch: Natural Science Foundation of Jiangsu Province BK20221355,BK20231521
Gefördert durch: National Natural Science Foundation of China 22322108

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Abstract A highly selective nickel-catalyzed monodefluorinative alkylcarbonylation between α-trifluoromethyl substituted styrenes and alkylzinc pivalates under 1 atm of CO gas is disclosed, thus providing an expedient approach to the synthesis of polyfunctionalized gem-difluoroalkenes under mild reaction conditions. Control experiments highlight the superior reactivity of alkylzinc pivalates compared to the conversional alkylzinc halides. Moreover, this method is distinguished by its ample scope and facile derivatizations of the resulting products for increasing functional molecular complexity via sequence defluorinative strategy.

Publikationsverlauf

Eingereicht: 26. April 2025

Angenommen nach Revision: 20. Mai 2025

Accepted Manuscript online:
20. Mai 2025

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