{"title":"Electrochemical 1,2-hydrogen atom transfer functionalizations of N-(benzyloxy)phthalimides†","authors":"Xin Fu , Tingting Ran , Jie Liu","doi":"10.1039/d4qo01607f","DOIUrl":null,"url":null,"abstract":"<div><div>We report a straightforward, catalyst-free method for the cathodic benzylic C–H hydroxyalkylation/arylation of <em>N</em>-(alkyloxy)phthalimides with ketones or cyanopyridines. The reaction is driven by an electrochemically induced 1,2-hydrogen atom transfer involving alkoxy radicals generated by O–N bond cleavage. This protocol provides an efficient approach for the synthesis of a wide range of valuable unsymmetrical 1,2-diols and diarylmethanols.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"11 23","pages":"Pages 6760-6767"},"PeriodicalIF":0.0000,"publicationDate":"2024-10-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412924006995","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/10/5 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
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Abstract
We report a straightforward, catalyst-free method for the cathodic benzylic C–H hydroxyalkylation/arylation of N-(alkyloxy)phthalimides with ketones or cyanopyridines. The reaction is driven by an electrochemically induced 1,2-hydrogen atom transfer involving alkoxy radicals generated by O–N bond cleavage. This protocol provides an efficient approach for the synthesis of a wide range of valuable unsymmetrical 1,2-diols and diarylmethanols.
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