{"title":"Electrocatalytic Enantioselective Tandem C–H Indolization toward Biindolyl Atropisomers: Reaction Development and Mechanistic Insight","authors":"Zhi-Huan Peng, Ping Huang, Ai’ran Li, Mingkai Yang, Zhikang Li, Yuanyuan Li, Shi Qin, Jiating Cai, Shengdong Wang, Zhi Zhou, Wei Yi, Hui Gao, Zhongyi Zeng","doi":"10.1021/acscatal.4c06594","DOIUrl":null,"url":null,"abstract":"The electrochemical methods for asymmetric indolization are still elusive and pose a significant challenge. Taking advantage of 2-alkynylanilines as electrochemically compatible indolyl equivalents, we herein represent a mild and highly enantioselective electrocatalytic process for tandem C–H indolization to form 2,3′-biindolyl atropisomers along with hydrogen evolution reaction. Integrated experimental and computational mechanistic studies revealed that a sequential C–H metalation/nucleophilic cyclization/reductive elimination/anodic oxidation sequence involving a Rh<sup>III</sup>–Rh<sup>I</sup>–Rh<sup>III</sup> catalytic cycle accounts for the established transformation.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"494 1","pages":""},"PeriodicalIF":11.3000,"publicationDate":"2025-01-09","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.4c06594","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
The electrochemical methods for asymmetric indolization are still elusive and pose a significant challenge. Taking advantage of 2-alkynylanilines as electrochemically compatible indolyl equivalents, we herein represent a mild and highly enantioselective electrocatalytic process for tandem C–H indolization to form 2,3′-biindolyl atropisomers along with hydrogen evolution reaction. Integrated experimental and computational mechanistic studies revealed that a sequential C–H metalation/nucleophilic cyclization/reductive elimination/anodic oxidation sequence involving a RhIII–RhI–RhIII catalytic cycle accounts for the established transformation.
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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