Ligand-Controlled Copper-Catalyzed Regiodivergent Sulfonylation of Yne-Vinyl Allylic Esters with Sodium Sulfinates

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-01-27 DOI:10.1021/acscatal.4c07043

Hui Zhu, Mingxin Shen, Zi-Han Wang, Genping Huang, Tao-Yan Lin

引用次数: 0

Abstract

Herein, we report the first ligand-controlled copper-catalyzed regiodivergent sulfonylation of yne-vinyl allylic esters with sodium sulfinates. The practicality and attractiveness of this protocol are showcased using readily available starting materials, mild reaction conditions, good regio- and stereoselectivities, and a broad substrate scope. A series of controlled experiments identified a copper divinyl-allenylidene complex as the key intermediate in this reaction. Density functional theory calculations delineate distinct mechanistic pathways for each nucleophilic addition step and elucidate their regioselectivity.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.