Si-Jing Jiang , Zhao-Zhao Li , Li-Na Yang , Ming Bian , Xiao-Han Qiu , Yu-Ning Gao , Hui-Yu Chen , Zhen-Jiang Liu
{"title":"羟基/氨基苯丙醇与氟烷磺酰氯的无金属异位重排/环化/芳构化级联反应：3 -氟烷磺酰苯并呋喃和吲哚的合成","authors":"Si-Jing Jiang , Zhao-Zhao Li , Li-Na Yang , Ming Bian , Xiao-Han Qiu , Yu-Ning Gao , Hui-Yu Chen , Zhen-Jiang Liu","doi":"10.1039/d5qo00107b","DOIUrl":null,"url":null,"abstract":"<div><div>A metal-free protocol to synthesize 2-alkyl-3-fluoroalkanesulfonyl benzofurans and indoles from <em>o</em>-hydroxyphenyl/<em>o</em>-aminophenyl propargyl alcohols or 2-propynolphenols/2-propynolanilines and fluoroalkanesulfinyl chlorides (R<sub>F</sub>SOCl) was disclosed. The mechanism is proposed to involve a sequential [1,2]/[2,3]-sigmatropic rearrangement/intramolecular oxy-addition/1,3-H migration cascade of propargyl triflinates generated <em>in situ via O</em>-fluoroalkanesulfinylation of propargyl alcohols. The procedure utilizes readily available propargyl alcohols and R<sub>F</sub>SOCl as starting materials and offers a broad substrate scope with excellent performance (55 examples, up to 98% yield).</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 9","pages":"Pages 2920-2925"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A metal-free sigmatropic rearrangement/cyclization/aromatization cascade reaction of hydroxy/aminophenyl propargyl alcohols with fluoroalkanesulfinyl chlorides: synthesis of 3-fluoroalkanesulfonyl benzofurans and indoles†\",\"authors\":\"Si-Jing Jiang , Zhao-Zhao Li , Li-Na Yang , Ming Bian , Xiao-Han Qiu , Yu-Ning Gao , Hui-Yu Chen , Zhen-Jiang Liu\",\"doi\":\"10.1039/d5qo00107b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A metal-free protocol to synthesize 2-alkyl-3-fluoroalkanesulfonyl benzofurans and indoles from <em>o</em>-hydroxyphenyl/<em>o</em>-aminophenyl propargyl alcohols or 2-propynolphenols/2-propynolanilines and fluoroalkanesulfinyl chlorides (R<sub>F</sub>SOCl) was disclosed. The mechanism is proposed to involve a sequential [1,2]/[2,3]-sigmatropic rearrangement/intramolecular oxy-addition/1,3-H migration cascade of propargyl triflinates generated <em>in situ via O</em>-fluoroalkanesulfinylation of propargyl alcohols. The procedure utilizes readily available propargyl alcohols and R<sub>F</sub>SOCl as starting materials and offers a broad substrate scope with excellent performance (55 examples, up to 98% yield).</div></div>\",\"PeriodicalId\":94379,\"journal\":{\"name\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"volume\":\"12 9\",\"pages\":\"Pages 2920-2925\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2025-02-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic chemistry frontiers : an international journal of organic chemistry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2052412925001433\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/2/22 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925001433","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/22 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
A metal-free sigmatropic rearrangement/cyclization/aromatization cascade reaction of hydroxy/aminophenyl propargyl alcohols with fluoroalkanesulfinyl chlorides: synthesis of 3-fluoroalkanesulfonyl benzofurans and indoles†
A metal-free protocol to synthesize 2-alkyl-3-fluoroalkanesulfonyl benzofurans and indoles from o-hydroxyphenyl/o-aminophenyl propargyl alcohols or 2-propynolphenols/2-propynolanilines and fluoroalkanesulfinyl chlorides (RFSOCl) was disclosed. The mechanism is proposed to involve a sequential [1,2]/[2,3]-sigmatropic rearrangement/intramolecular oxy-addition/1,3-H migration cascade of propargyl triflinates generated in situ via O-fluoroalkanesulfinylation of propargyl alcohols. The procedure utilizes readily available propargyl alcohols and RFSOCl as starting materials and offers a broad substrate scope with excellent performance (55 examples, up to 98% yield).
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