{"title":"Ru(II)-Catalyzed ortho-Vinylation of Benzoic Acids in Water","authors":"Lalit Negi, Aditi Soni, Deepak Sharma, Manisha Manisha, Raj K. Joshi","doi":"10.1021/acs.joc.4c00948","DOIUrl":null,"url":null,"abstract":"Herein, we report an efficient [Ru(η<sup>6</sup>-C<sub>6</sub>H<sub>6</sub>)Cl<sub>2</sub>]<sub>2</sub> catalyzed oxidative C–H alkenylation of benzoic acid in the green solvent water. A regioselective olefination of benzoic acid with functionalized alkenes like styrene and acrylate was established at a very mild condition of 60 °C temperature and in an aqueous medium. In contrast to the cyclization of the carboxylic group, a selective <i>ortho</i>-olefination product of benzoic acid was observed with the acrylate. Moreover, a selective formation of mono-olefinated products were observed with activated olefins (acrylate), while mono and diolefinated products were recorded with unactivated olefins (styrene). In contrast to the reactivity of acrylates and styrenes, a fruitful development and formation of a novel five-member cyclic ring, i.e., the (<i>Z</i>)-3-ferrocenylideneisobenzofuran-1(3<i>H</i>)-one, was observed when vinylferrocene was considered as a coupling partner for the reaction.","PeriodicalId":57,"journal":{"name":"Journal of Organic Chemistry","volume":"73 1","pages":""},"PeriodicalIF":3.6000,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Organic Chemistry","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1021/acs.joc.4c00948","RegionNum":2,"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 an efficient [Ru(η6-C6H6)Cl2]2 catalyzed oxidative C–H alkenylation of benzoic acid in the green solvent water. A regioselective olefination of benzoic acid with functionalized alkenes like styrene and acrylate was established at a very mild condition of 60 °C temperature and in an aqueous medium. In contrast to the cyclization of the carboxylic group, a selective ortho-olefination product of benzoic acid was observed with the acrylate. Moreover, a selective formation of mono-olefinated products were observed with activated olefins (acrylate), while mono and diolefinated products were recorded with unactivated olefins (styrene). In contrast to the reactivity of acrylates and styrenes, a fruitful development and formation of a novel five-member cyclic ring, i.e., the (Z)-3-ferrocenylideneisobenzofuran-1(3H)-one, was observed when vinylferrocene was considered as a coupling partner for the reaction.
期刊介绍：
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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