Mengran Gan , Xiaoting Wu , Xiaochen Ji , Huawen Huang
{"title":"溴通过光氧化还原催化促进异氰酸双芳烯与醛的级联环。","authors":"Mengran Gan , Xiaoting Wu , Xiaochen Ji , Huawen Huang","doi":"10.1039/d4ob02085e","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes <em>via</em> photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions. Its synthetic utility was demonstrated by a gram-scale reaction and various facile manipulations of the free hydroxyl group to furnish diverse phenanthridine derivatives.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 9","pages":"Pages 2101-2105"},"PeriodicalIF":2.8000,"publicationDate":"2025-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Bromide-promoted cascade annulation of isocyanobiaryls with aldehydes through photoredox catalysis†\",\"authors\":\"Mengran Gan , Xiaoting Wu , Xiaochen Ji , Huawen Huang\",\"doi\":\"10.1039/d4ob02085e\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes <em>via</em> photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions. Its synthetic utility was demonstrated by a gram-scale reaction and various facile manipulations of the free hydroxyl group to furnish diverse phenanthridine derivatives.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 9\",\"pages\":\"Pages 2101-2105\"},\"PeriodicalIF\":2.8000,\"publicationDate\":\"2025-01-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052025000655\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/22 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025000655","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/22 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Bromide-promoted cascade annulation of isocyanobiaryls with aldehydes through photoredox catalysis†
Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes via photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions. Its synthetic utility was demonstrated by a gram-scale reaction and various facile manipulations of the free hydroxyl group to furnish diverse phenanthridine derivatives.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.