{"title":"Ru(II)-Catalyzed Sustainable C-H Methylation of Indolines with Organoboranes in Ethanol.","authors":"Sumit, Sachin, Devesh Chandra, Upendra Sharma","doi":"10.1021/acs.joc.4c01650","DOIUrl":null,"url":null,"abstract":"<p><p>A sustainable protocol for Ru(II)-catalyzed regioselective C(sp<sup>2</sup>)-H methylation of indolines in the presence of ethanol has been explored. A wide array of substituted indolines were successfully methylated <i>via</i> the developed protocol with good to excellent yields. Deuterium labeling experiments suggested the reversible nature of the C-H activation step. Kinetic isotope effect studies revealed that C-H activation might be the rate-determining step. Gram scale reaction and post-transformation reactions of the methylated product demonstrated the potential of the developed protocol.</p>","PeriodicalId":57,"journal":{"name":"The Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"The Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c01650","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/9/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A sustainable protocol for Ru(II)-catalyzed regioselective C(sp2)-H methylation of indolines in the presence of ethanol has been explored. A wide array of substituted indolines were successfully methylated via the developed protocol with good to excellent yields. Deuterium labeling experiments suggested the reversible nature of the C-H activation step. Kinetic isotope effect studies revealed that C-H activation might be the rate-determining step. Gram scale reaction and post-transformation reactions of the methylated product demonstrated the potential of the developed protocol.
期刊介绍：
The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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