{"title":"Photoredox/Nickel Dual-Catalyzed Deaminative Cross-Electrophile for Allenylic Alkylation with Non-Activated Alkyl Katritzky Salts","authors":"Zhao-Zhao Zhou, Xiao-Feng Zhai, Ke-Jian Xia, Xian-Rong Song, Haixin Ding, Wan-Fa Tian, Shu-Liang Zhang, Yong-Min Liang, Qiang Xiao","doi":"10.1039/d4qo00834k","DOIUrl":null,"url":null,"abstract":"Herein, we report the first allenylic alkylation with bench-stable aliphatic amine derivatives Katritzky salts via photoredox/nickel dual-catalyzed reductive deaminative cross-electrophile coupling. Non-activated alkyl has been efficiently introduced and abundant substrate sources made the reaction more alternative and widely applicable, which avoiding the limitations from rare allenylic alkylations with amino acid derivatives. Meanwhile, the successful involvement of alkyl propargylic electrophiles also represents the rare direct approach for polyalkylated allenes without organometallic reagents. Mechanically, a hypothetical radical-radical coupling between alkyl radical and hybrid allenyl-Ni(I) radical species is proposed.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00834k","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we report the first allenylic alkylation with bench-stable aliphatic amine derivatives Katritzky salts via photoredox/nickel dual-catalyzed reductive deaminative cross-electrophile coupling. Non-activated alkyl has been efficiently introduced and abundant substrate sources made the reaction more alternative and widely applicable, which avoiding the limitations from rare allenylic alkylations with amino acid derivatives. Meanwhile, the successful involvement of alkyl propargylic electrophiles also represents the rare direct approach for polyalkylated allenes without organometallic reagents. Mechanically, a hypothetical radical-radical coupling between alkyl radical and hybrid allenyl-Ni(I) radical species is proposed.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.