Work

Rapid assembly of enantioenriched α-arylated ketones via Ni-catalyzed asymmetric cross-hydrocarbonylation enabled by alkene sorting

Year: 2025

Type: article

Abstract: Enantioenriched α-arylated dialkyl ketones with acidic proton are ubiquitous subunits in valuable target organic molecules and serve as versatile synthetic precursors for other value-added chiral blocks. Herein, a distinct synthetic strategy of enantioenriched α-arylated dialkyl ketones enabled by nickel-catalyzed iterative cross-hydrocarbonylation of two alkenes has been developed, representing a reaction mode for the direct synthesis of asymmetric α-arylated dialkyl ketones. One aliphatic alkene and one styrene are creatively used as surrogates of two different alkyl precursors. Two different alkenes are sewed together by a “carbonyl glue” with exclusive alkene sorting. This straightforward and gas-free protocol transforms a diverse array of styrene and unactivated alkenes into highly valuable α-arylated dialkyl ketones with high levels of enantioselectivity, allowing for the construction of enantioenriched unsymmetric dialkyl ketones from only alkenes. This process is also applicable to late-stage functionalization of complex molecules. Enantioenriched α-arylated dialkyl ketones with acidic proton are ubiquitous subunits in organic molecules and serve as synthetic precursors for other value-added chiral blocks. Here, the authors report a synthetic strategy of enantioenriched α-arylated dialkyl ketones enabled by nickel-catalyzed iterative cross-hydrocarbonylation of two alkenes.

Source: Nature Communications

DOI: 10.1038/s41467-025-57967-4

Authors: Yi-Ming Du, Xiao-Yi Chen, Yulong Li, Ming Joo Koh, Wei Shu

Institutions: Southern University of Science and Technology, Sichuan University of Science and Engineering, National University of Singapore

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,990