{"title":"以2 -巯基噻唑盐为烷基自由基源,可见光催化合成烷基化吲哚[2,1-α]异喹啉","authors":"Chi-Fan Zhu, Fei Li, Jun-Ju Mai, Xiao-Jing Li, Xiasen Dong, Mingyuan Shi, Mei-Hua Shen, Hua-Dong Xu","doi":"10.1016/j.tetlet.2024.155397","DOIUrl":null,"url":null,"abstract":"<div><div>A visible-light-induced radical cascade cyclization of 2-aryl-<em>N</em>-acryloyl indoles with 2‑mercaptothiazolinium salts is reported, furnishing the corresponding indolo[2,1-<em>α</em>]isoquinoline derivatives in good to moderate yields. A series of primary, secondary, and tertiary alkyl bromides were converted conveniently into redox-active thiazolinium salts, which are subsequently transformed into alkyl radicals through interaction with an excited-state photocatalyst. This green and environmentally protocol features broad substrate scope under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155397"},"PeriodicalIF":1.5000,"publicationDate":"2024-11-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible-light-promoted synthesis of alkylated Indolo[2,1-α]isoquinolines using 2‑Mercaptothiazolinium salts as alkyl radical source\",\"authors\":\"Chi-Fan Zhu, Fei Li, Jun-Ju Mai, Xiao-Jing Li, Xiasen Dong, Mingyuan Shi, Mei-Hua Shen, Hua-Dong Xu\",\"doi\":\"10.1016/j.tetlet.2024.155397\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A visible-light-induced radical cascade cyclization of 2-aryl-<em>N</em>-acryloyl indoles with 2‑mercaptothiazolinium salts is reported, furnishing the corresponding indolo[2,1-<em>α</em>]isoquinoline derivatives in good to moderate yields. A series of primary, secondary, and tertiary alkyl bromides were converted conveniently into redox-active thiazolinium salts, which are subsequently transformed into alkyl radicals through interaction with an excited-state photocatalyst. This green and environmentally protocol features broad substrate scope under mild conditions.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"154 \",\"pages\":\"Article 155397\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2024-11-29\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403924004921\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403924004921","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
报道了一种可见光诱导的2-芳基- n -丙烯酰吲哚与2巯基噻唑盐的自由基级联环化反应,得到了相应的吲哚[2,1-α]异喹啉衍生物。一系列的伯、仲、叔烷基溴被方便地转化为氧化还原活性的噻唑盐,随后通过与激发态光催化剂的相互作用转化为烷基自由基。这种绿色环保的协议在温和的条件下具有广泛的基材范围。
Visible-light-promoted synthesis of alkylated Indolo[2,1-α]isoquinolines using 2‑Mercaptothiazolinium salts as alkyl radical source
A visible-light-induced radical cascade cyclization of 2-aryl-N-acryloyl indoles with 2‑mercaptothiazolinium salts is reported, furnishing the corresponding indolo[2,1-α]isoquinoline derivatives in good to moderate yields. A series of primary, secondary, and tertiary alkyl bromides were converted conveniently into redox-active thiazolinium salts, which are subsequently transformed into alkyl radicals through interaction with an excited-state photocatalyst. This green and environmentally protocol features broad substrate scope under mild conditions.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.