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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
1   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)
,
Hao Yuan
1   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)
,
Changrui Nie
1   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)
,
Shulei Ge
1   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)
,
Jie Li 
1   College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China (Ringgold ID: RIN12582)
› Author AffiliationsSupported by: Jiangsu Specially Appointed Professors Plan SR10900122
Supported by: Natural Science Foundation of Jiangsu Province BK20221355,BK20231521
Supported by: 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.



Publication History

Received: 26 April 2025

Accepted after revision: 20 May 2025

Accepted Manuscript online:
20 May 2025

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