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<scp>Nickel‐Catalyzed</scp> Regiodivergent Acylzincation of Styrenes with Organozincs and <scp>CO</scp><sup>†</sup>

Chenglong Wang, Ning Liu, Xianqing Wu, Jingping Qü, Yifeng Chen

2023Chinese Journal of Chemistry12 citationsDOIOpen Access PDF

Abstract

Comprehensive Summary Transition metal‐catalyzed carbometallation of unsaturated hydrocarbons constitutes one of the most efficient synthetic methodologies for the construction of C—C bond. Recently, the incorporation of organometallic reagent with the CO gas as a nucleophilic acyl synthon could enable the acylmetallation reaction, which greatly increases the horizon of carbometallation chemistry. Herein, we report a nickel‐catalyzed regiodivergent acylzincation of o ‐cyano cinnamate ester and o ‐cyano styrene, in which the cyano moiety intramolecularly captures zinc intermediates to trigger the tandem cyclization process. This protocol features mild conditions, broad substrate scope and excellent functional group tolerance, thus affording a diverse array of highly functionalized carbocyclic compounds.

Topics & Concepts

ChemistryCatalysisSynthonReagentMoietyNickelNucleophileSubstrate (aquarium)Combinatorial chemistryTransition metalTandemTriple bondFunctional groupMedicinal chemistryOrganic chemistryDouble bondMaterials scienceOceanographyPolymerGeologyComposite materialCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSulfur-Based Synthesis Techniques
<scp>Nickel‐Catalyzed</scp> Regiodivergent Acylzincation of Styrenes with Organozincs and <scp>CO</scp><sup>†</sup> | Litcius