{"title":"Amino Alcohol Ligand-enabled Ni-Catalyzed Regio- and Diastereoselective Dearomative Borylalkylation of Indoles","authors":"Jiaxin Wang, Xuelong Zhang, Aichen Li, Rui He, Surong Zhang, Xiangyue Li, Lanlan Zhang, Guodong Ju, Chao Wang","doi":"10.1039/d4qo02187h","DOIUrl":null,"url":null,"abstract":"The transition-metal-catalyzed intermolecular three-component dearomative difunctionalization of indoles in a one-pot fashion remains largely unexplored. Herein, we present a novel Ni-catalyzed dearomative alkylborylation of indoles utilizing a ligand-enabled, directing group-assisted strategy. This regio- and diastereoselective reaction efficiently converts readily accessible indoles into valuable C3-borylated and C2-alkylated indolines. Additionally, We established a practical one-pot procedure for accessing valuable 2,3-disubstituted indoles with boron retained by combining this protocol with the subsequent oxidation of the resulting indolines. The robustness of this protocol is demonstrated through gram-scale reactions, facile late-stage decoration of complex drug-like molecules, and various downstream diversifications.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"83 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-12-24","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/d4qo02187h","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
The transition-metal-catalyzed intermolecular three-component dearomative difunctionalization of indoles in a one-pot fashion remains largely unexplored. Herein, we present a novel Ni-catalyzed dearomative alkylborylation of indoles utilizing a ligand-enabled, directing group-assisted strategy. This regio- and diastereoselective reaction efficiently converts readily accessible indoles into valuable C3-borylated and C2-alkylated indolines. Additionally, We established a practical one-pot procedure for accessing valuable 2,3-disubstituted indoles with boron retained by combining this protocol with the subsequent oxidation of the resulting indolines. The robustness of this protocol is demonstrated through gram-scale reactions, facile late-stage decoration of complex drug-like molecules, and various downstream diversifications.
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.