{"title":"Dynamic Kinetic Reductive Grignard-Type Addition for the Construction of Axial and Central Chirality","authors":"Ya-Ping Shao, Yong-Min Liang","doi":"10.1021/acscatal.4c07172","DOIUrl":null,"url":null,"abstract":"This study describes a photoredox/cobalt dual-catalyzed asymmetric Grignard-type addition reaction, enabling the synthesis of axially chiral hexatomic (six–six) N-heterobiaryls bearing the extra chiral secondary alcohol unit via an efficient dynamic kinetic asymmetric transformation of racemic N-heterobiaryl triflate substrates. The conversion facilitated via both photoredox and classical reductive reaction conditions exhibits good functional group tolerance, a broad substrate scope, and satisfactory stereoselectivity. Furthermore, control experiments and density functional theory calculations provide preliminary mechanistic insights.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"34 1","pages":""},"PeriodicalIF":11.3000,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c07172","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
This study describes a photoredox/cobalt dual-catalyzed asymmetric Grignard-type addition reaction, enabling the synthesis of axially chiral hexatomic (six–six) N-heterobiaryls bearing the extra chiral secondary alcohol unit via an efficient dynamic kinetic asymmetric transformation of racemic N-heterobiaryl triflate substrates. The conversion facilitated via both photoredox and classical reductive reaction conditions exhibits good functional group tolerance, a broad substrate scope, and satisfactory stereoselectivity. Furthermore, control experiments and density functional theory calculations provide preliminary mechanistic insights.
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.
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