{"title":"镍催化烯系吲哚与磺酰氯的环化/硫代羰基化反应:硫酯取代的吲哚并[2,1-a]异喹啉的合成","authors":"Chen-Yang Hou , Hucheng Ma , Ruyi Zhao , Xinxin Qi , Xiao-Feng Wu","doi":"10.1016/j.jcat.2024.115765","DOIUrl":null,"url":null,"abstract":"<div><p>A novel and straightforward procedure for the synthesis of thioester-substituted indolo[2,1-<em>a</em>]isoquinolines has been established. The reaction proceed <em>via</em> nickel-catalyzed cyclization/thiocarbonylation from alkene-tethered indoles and sulfonyl chlorides. Very good compatibility toward a wide range of functional groups was observed, both aryl and alkyl sulfonyl chlorides were well tolerated. With Mo(CO)<sub>6</sub> as a convenient and solid CO surrogate, and by using sulfonyl chloride as an abundant and cheap sulfur source, a variety of thioester-substituted indolo[2,1-<em>a</em>]isoquinolines were obtained in moderate to high yields.</p></div>","PeriodicalId":346,"journal":{"name":"Journal of Catalysis","volume":"439 ","pages":"Article 115765"},"PeriodicalIF":6.5000,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Nickel-Catalyzed Cyclization/Thiocarbonylation of Alkene-Tethered indoles with sulfonyl Chlorides: Synthesis of Thioester-Substituted Indolo[2,1-a]isoquinolines\",\"authors\":\"Chen-Yang Hou , Hucheng Ma , Ruyi Zhao , Xinxin Qi , Xiao-Feng Wu\",\"doi\":\"10.1016/j.jcat.2024.115765\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A novel and straightforward procedure for the synthesis of thioester-substituted indolo[2,1-<em>a</em>]isoquinolines has been established. The reaction proceed <em>via</em> nickel-catalyzed cyclization/thiocarbonylation from alkene-tethered indoles and sulfonyl chlorides. Very good compatibility toward a wide range of functional groups was observed, both aryl and alkyl sulfonyl chlorides were well tolerated. With Mo(CO)<sub>6</sub> as a convenient and solid CO surrogate, and by using sulfonyl chloride as an abundant and cheap sulfur source, a variety of thioester-substituted indolo[2,1-<em>a</em>]isoquinolines were obtained in moderate to high yields.</p></div>\",\"PeriodicalId\":346,\"journal\":{\"name\":\"Journal of Catalysis\",\"volume\":\"439 \",\"pages\":\"Article 115765\"},\"PeriodicalIF\":6.5000,\"publicationDate\":\"2024-09-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0021951724004780\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0021951724004780","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
摘要
一种新颖而简单的硫酯取代吲哚并[2,1-a]异喹啉合成方法已经建立。该反应是通过镍催化的环化/硫代羰基化反应从烯系吲哚和磺酰氯中进行的。该反应对多种官能团都有很好的相容性,对芳基和烷基磺酰氯都有很好的耐受性。利用 Mo(CO)6 作为方便的固体 CO 代用品,并使用磺酰氯作为丰富而廉价的硫源,以中等至高产率获得了多种硫酯取代的吲哚并[2,1-a]异喹啉。
Nickel-Catalyzed Cyclization/Thiocarbonylation of Alkene-Tethered indoles with sulfonyl Chlorides: Synthesis of Thioester-Substituted Indolo[2,1-a]isoquinolines
A novel and straightforward procedure for the synthesis of thioester-substituted indolo[2,1-a]isoquinolines has been established. The reaction proceed via nickel-catalyzed cyclization/thiocarbonylation from alkene-tethered indoles and sulfonyl chlorides. Very good compatibility toward a wide range of functional groups was observed, both aryl and alkyl sulfonyl chlorides were well tolerated. With Mo(CO)6 as a convenient and solid CO surrogate, and by using sulfonyl chloride as an abundant and cheap sulfur source, a variety of thioester-substituted indolo[2,1-a]isoquinolines were obtained in moderate to high yields.
期刊介绍:
The Journal of Catalysis publishes scholarly articles on both heterogeneous and homogeneous catalysis, covering a wide range of chemical transformations. These include various types of catalysis, such as those mediated by photons, plasmons, and electrons. The focus of the studies is to understand the relationship between catalytic function and the underlying chemical properties of surfaces and metal complexes.
The articles in the journal offer innovative concepts and explore the synthesis and kinetics of inorganic solids and homogeneous complexes. Furthermore, they discuss spectroscopic techniques for characterizing catalysts, investigate the interaction of probes and reacting species with catalysts, and employ theoretical methods.
The research presented in the journal should have direct relevance to the field of catalytic processes, addressing either fundamental aspects or applications of catalysis.