{"title":"Preparation of naphthalenes via Pd-catalyzed annulation of 5-(2-bromophenyl)pent-3-en-1-ynes under Suzuki-Miyaura coupling conditions","authors":"Cheng-Kai Hsu, Yi-Hung Liu, Shiuh-Tzung Liu","doi":"10.1002/jccs.202400215","DOIUrl":null,"url":null,"abstract":"<p>Highly substituted naphthalene derivatives were prepared via palladium-catalyzed reaction of 5-(2-bromophenyl)pent-3-en-1-ynes with arylboronic acids. Typically, reaction of 3-bromo-4-(3-(4-chlorophenyl)-5-phenyl-1-(<i>p</i>-tolyl)pent-2-en-4-yn-1-yl)-<i>N</i>-methylaniline (<b>1a</b>) with PhB(OH)<sub>2</sub> in the presence of Pd(PPh<sub>3</sub>)<sub>4</sub> as the catalyst under basic conditions provided 8-benzhydryl-7-(4-chlorophenyl)-<i>N</i>-methyl-5-(<i>p-</i>tolyl)naphthalen-2-amine (<b>2a</b>) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of <b>2j</b> was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.</p>","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jccs.202400215","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Highly substituted naphthalene derivatives were prepared via palladium-catalyzed reaction of 5-(2-bromophenyl)pent-3-en-1-ynes with arylboronic acids. Typically, reaction of 3-bromo-4-(3-(4-chlorophenyl)-5-phenyl-1-(p-tolyl)pent-2-en-4-yn-1-yl)-N-methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8-benzhydryl-7-(4-chlorophenyl)-N-methyl-5-(p-tolyl)naphthalen-2-amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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