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

Synthesis, Inhaltsverzeichnis

Synthesis 2025; 57(21): 3341-3349
DOI: 10.1055/a-2617-6013

Paper

Published as part of the Special Topic Dedicated to Prof. Paul Knochel

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

Autor*innen

Donghao Luo

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China
Hao Yuan

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China
Changrui Nie

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China
Shulei Ge

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China
Jie Li

College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, China

Abstract

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Dedication

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

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 convensional alkylzinc halides. Moreover, this method is distinguished by its ample scope and facile derivatization of the resulting products for increasing functional molecular complexity via a sequential defluorinative strategy.

Keywords

Carbonylation - Monodefluorination - Gem-difluoroalkenes - Nickel catalysis - Ketones

Volltext

Referenzen

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