Isabelle C Bote, Zoe A Krevlin, Maria Christina F Crespo, Sudchananya Udomphan, Carolyn T Levin, Christie C Lam, Amy M Glanzer, Holly L Hutchinson, Alisha M Blades, Danielle L McConnell, Crystal Lin, John P Frank, William R Strutton, Jordan C Merklin, Beau A Sinardo, Khady J Gueye, Karly V Leiman, Ashley Thayaparan, Joel K A Adade, Nestor L Martinez, Wesley W Kramer, Max M Majireck
{"title":"Bench-Stable 2-Halopyridinium Ketene Hemiaminals as Reagents for the Synthesis of 2-Aminopyridine Derivatives.","authors":"Isabelle C Bote, Zoe A Krevlin, Maria Christina F Crespo, Sudchananya Udomphan, Carolyn T Levin, Christie C Lam, Amy M Glanzer, Holly L Hutchinson, Alisha M Blades, Danielle L McConnell, Crystal Lin, John P Frank, William R Strutton, Jordan C Merklin, Beau A Sinardo, Khady J Gueye, Karly V Leiman, Ashley Thayaparan, Joel K A Adade, Nestor L Martinez, Wesley W Kramer, Max M Majireck","doi":"10.1021/acs.orglett.4c02915","DOIUrl":null,"url":null,"abstract":"<p><p>2-Chloro-1-(1-ethoxyvinyl)pyridinium triflate and several other bench-stable <i>N</i>-(1-alkoxyvinyl) 2-halopyridinium triflates have been developed as reagents for the synthesis of valuable 2-aminopyridine scaffolds via unusually mild S<sub>N</sub>Ar substitutions with amine nucleophiles. Advantages of this approach include an operationally simple mix-and-stir procedure at room temperature or mild heat and ambient atmosphere and without the need for transition metal catalysts, coupling reagents, or high-boiling solvents. The stable <i>N</i>-(1-ethoxyvinyl) moiety serves as a dual S<sub>N</sub>Ar-activating group and pyridine <i>N</i>-protecting group that can be cleaved under thermal, acidic, or oxidative conditions. Preliminary results of other nucleophilic substitutions using oxygen-, sulfur-, and carbon-based nucleophiles are also demonstrated.</p>","PeriodicalId":4,"journal":{"name":"ACS Applied Energy Materials","volume":null,"pages":null},"PeriodicalIF":5.4000,"publicationDate":"2024-09-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Energy Materials","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c02915","RegionNum":3,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
2-Chloro-1-(1-ethoxyvinyl)pyridinium triflate and several other bench-stable N-(1-alkoxyvinyl) 2-halopyridinium triflates have been developed as reagents for the synthesis of valuable 2-aminopyridine scaffolds via unusually mild SNAr substitutions with amine nucleophiles. Advantages of this approach include an operationally simple mix-and-stir procedure at room temperature or mild heat and ambient atmosphere and without the need for transition metal catalysts, coupling reagents, or high-boiling solvents. The stable N-(1-ethoxyvinyl) moiety serves as a dual SNAr-activating group and pyridine N-protecting group that can be cleaved under thermal, acidic, or oxidative conditions. Preliminary results of other nucleophilic substitutions using oxygen-, sulfur-, and carbon-based nucleophiles are also demonstrated.
期刊介绍:
ACS Applied Energy Materials is an interdisciplinary journal publishing original research covering all aspects of materials, engineering, chemistry, physics and biology relevant to energy conversion and storage. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials, engineering, physics, bioscience, and chemistry into important energy applications.