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.
{"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":"10.1002/jccs.202400215","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":17262,"journal":{"name":"Journal of The Chinese Chemical Society","volume":"71 10","pages":"1300-1308"},"PeriodicalIF":1.6,"publicationDate":"2024-08-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142213610","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Preview: Journal of the Chinese Chemical Society 08/2024","authors":"","doi":"10.1002/jccs.202408001","DOIUrl":"https://doi.org/10.1002/jccs.202408001","url":null,"abstract":"","PeriodicalId":17262,"journal":{"name":"Journal of The Chinese Chemical Society","volume":"71 8","pages":"942"},"PeriodicalIF":1.6,"publicationDate":"2024-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/jccs.202408001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142021803","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This special issue on “Frontier Precise Measurement” aims to highlight the latest developments and applications in this dynamic area of research. In this special issue, we have invited chemists from a broad range of disciplines and expertise to showcase the diversity and activity of chemical and biological measurement. The issue features a diverse collection of articles covering various topics in precision measurement, including extraction, spectroscopy, sensors, electrochemical detection, mass spectrometry, and software development. We hope that readers will thoroughly enjoy the content.