{"title":"室温下 2-芳基酚类化合物的定向基团控制的区域选择性 C-H 玻里化反应","authors":"Jiao Kang, Jing Liu and Zhilong Chen","doi":"10.1039/D4QO00805G","DOIUrl":null,"url":null,"abstract":"<p >Regioselective borylation of (hetero)arenes under mild conditions is an appealing strategy for constructing boron-containing compounds, particularly considering their broad applications in organic synthesis, medicinal chemistry and material science. In this manuscript, we developed a Fe(OTf)<small><sub>3</sub></small>-promoted, DG (directing group)-controlled, regioselective electrophilic C–H borylation of 2-arylphenolic compounds with BBr<small><sub>3</sub></small> at room temperature. C2′-borylation was dramatically accelerated by an LA-catalyst, affording DAOB (diaryloxaborin) with a broad substrate scope in moderate-to-excellent yields. The selective <em>ortho</em>-borylation was successfully achieved by introducing phenolic carbamate as a directing group to overcome the competing Fries rearrangement, giving desired 2-HAB ((2-hydroxyaryl)boronic acid) in good yields for most substrates.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Directing group controlled regioselective C–H borylation of 2-arylphenolic compounds at room temperature†\",\"authors\":\"Jiao Kang, Jing Liu and Zhilong Chen\",\"doi\":\"10.1039/D4QO00805G\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Regioselective borylation of (hetero)arenes under mild conditions is an appealing strategy for constructing boron-containing compounds, particularly considering their broad applications in organic synthesis, medicinal chemistry and material science. In this manuscript, we developed a Fe(OTf)<small><sub>3</sub></small>-promoted, DG (directing group)-controlled, regioselective electrophilic C–H borylation of 2-arylphenolic compounds with BBr<small><sub>3</sub></small> at room temperature. C2′-borylation was dramatically accelerated by an LA-catalyst, affording DAOB (diaryloxaborin) with a broad substrate scope in moderate-to-excellent yields. The selective <em>ortho</em>-borylation was successfully achieved by introducing phenolic carbamate as a directing group to overcome the competing Fries rearrangement, giving desired 2-HAB ((2-hydroxyaryl)boronic acid) in good yields for most substrates.</p>\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00805g\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00805g","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Directing group controlled regioselective C–H borylation of 2-arylphenolic compounds at room temperature†
Regioselective borylation of (hetero)arenes under mild conditions is an appealing strategy for constructing boron-containing compounds, particularly considering their broad applications in organic synthesis, medicinal chemistry and material science. In this manuscript, we developed a Fe(OTf)3-promoted, DG (directing group)-controlled, regioselective electrophilic C–H borylation of 2-arylphenolic compounds with BBr3 at room temperature. C2′-borylation was dramatically accelerated by an LA-catalyst, affording DAOB (diaryloxaborin) with a broad substrate scope in moderate-to-excellent yields. The selective ortho-borylation was successfully achieved by introducing phenolic carbamate as a directing group to overcome the competing Fries rearrangement, giving desired 2-HAB ((2-hydroxyaryl)boronic acid) in good yields for most substrates.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.